E-File Your Federal and State Tax Extension Online For FREE!

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Updated. The deadline for filing your federal taxes this year is Tuesday, April 15th, 2014. If you file for an extension, you will automatically be extended by six months to Wednesday, October 15, 2014. Here’s how to e-File a official federal extension with the IRS in minutes for free (plus state extensions too!). Why bother with paper and stamps – do it all online, avoid getting hit with penalties, and get confirmation of receipt within hours.

Option #1: TaxACT

This is how I did my extension for the last two years. Just sign up with TaxACT.com and e-file your extension for free through them. It’s quick. It’s easy. You don’t even need to actually use them to file your taxes later, although TaxACT is also free for federal taxes with e-File included regardless of income and $17.99 for state returns with e-File included.

(That’s cheaper than TurboTax or TaxCut, although if you’re already familiar with those programs it may be worth the extra bucks to stick with them, since you can save time by importing your previous year’s data.)

Directions
First, register for free at TaxACT.com with your e-mail address and pick a password. To go directly to the extension form, click on the “Filing” tab on the top, and then the “File Extension” link right below it (see below). You will then be guided through the Form 4868 in a question-and-answer format. You will then be able to have the form filed electronically instantly (or you can print and snail mail).

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If you don’t think you’ll owe any taxes, you can just put down zero as your expected tax liability. If you wish to make a tax payment, you will be able to choose to pay with direct withdrawal from a bank account (account and routing numbers required) or pay with a credit card (IRS fees apply).

Afterward, you can confirm the status of your extension e-file by going to efstatus.taxact.com. They will even send you a confirmation via e-mail or text message. I got my confirmation less than 3 hours after submission.

Free state tax extensions too! TaxACT will now even file out your state tax extension online if possible, otherwise they will provide guidance fill out all the paper form entries for you and all you have to do is print it out and mail it in. That’s how it worked for my state extension.

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Mortgage Interest Tax Deduction Doesn’t Help Homeownership?

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The mortgage interest tax deduction primarily helps the wealthy buy bigger houses rather than increase homeownership rates, according to a new study quoted by this WSJ article. The study found that such tax benefits have help increase the size of house by as much as 18% in affluent areas. Here is a graphic of the average annual tax savings from 10 major metro areas, broken down into households earning over and under $100,000 a year.

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My non-political thoughts:

Don’t overestimate the benefit of the mortgage tax deduction. It is easy to simply take your marginal tax bracket (say, 28%) and say that you’re saving 28% on all your mortgage interest. But mortgage interest is only tax-deductible if you itemize, which encompasses just 30-40% of Americans. Even then, you should consider the incremental savings above the standard deduction.

Everyone can take the standard deduction, which in 2014 is $12,400 for married filing joints and $6,200 for single filers. Let’s say your mortgage is for $250,000 and the interest rate is 4%. That’s $10,000 in interest annually. So far, the married folks have no tax benefit at all! You would need a lot of other deductions like state income tax, property tax, and charitable contributions to push you over the hump. For example if you have $7,400 in other deductions, then only half of your mortgage interest ($5,000 out of $10,000) is actually saving you anything extra in taxes.

Accordingly, the study quoted above also found that homeowners with incomes above $100,000 were between three and four times as likely to claim the tax benefit as those earning less than $100,000.

Even if you do itemize and have a high income (~$254k for single, ~$305k for married filing joint), look up the new Pease Limitation which reduces the value of various deductions including mortgage interest, state/local taxes, and charitable contributions.

Be prepared that the mortgage interest tax deduction may go away. I’m not going to talk about whether or not it should go away, but realistically there is a chance that it will. If it does disappear, it think it would be done gradually to prevent a shock to housing prices. However, I wouldn’t buy a house where I am depending on the tax deduction to maintain affordability. Tax laws change.

My prediction is that the mortgage interest tax deduction is still too popular to be completely nuked. Most likely there will be more legislation that nibbles around the edges like the mentioned Pease limitation that does a income phase-out or the total loan amount allowed will be reduced from the current $1,000,000 cap.

Tax Guide 2013 for LendingClub and Prosper 1099 Forms

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Updated 2014. I’ve gotten a few tax-filing questions regarding P2P lenders Prosper Lending and Lending Club. For tax year 2013, LendingClub provided individual investors extra guidance with their Tax Guide for Retail Investors [pdf]. Using this information, I have updated this post.

Don’t file too early. My first recommendation is to not print out or download any of your 1099s until mid-March. Both Prosper and LendingClub seem to regularly issue corrected and/or amended 1099 forms with new numbers late in February. If you already printed them out earlier, go back and make sure they haven’t been changed. After having to file an amended return a few years ago, I always wait until after mid-March to gather all my tax documents.

Where to find your tax documents. I don’t think either Prosper or Lendingclub sends you 1099 forms in the mail. The easiest way for me to direct you to these documents is for you to cut-and-paste the following URLs into your web browser and then log into your accounts. Here are screenshots of what the pages should look like for Prosper and LendingClub.

https://www.prosper.com/secure/account/common/statements.aspx

https://www.lendingclub.com/account/taxDocuments.action

Tax disclaimer. I am not a tax professional. The following is based on my best attempt at understanding the fuzzy world of P2P lending taxes. I am simply sharing how I’m going to do my personal tax return, but you should consult a tax professional for an expert opinion. You may not get all or most of these forms.

LendingClub

LendingClub 1099-OID. OID stands for original issue discount. The total of Box 1 is basically what LendingClub is reporting as the interest earned on your loans, net of fees. This interest should be reported on Schedule B and taxed as ordinary interest income (similar to interest from bank accounts).

LendingClub 1099-B (Recoveries for Charge-offs). If you had any loans charged-off*, but they still recovered some money later on, that will be reported here. It should be broken down into either short-term or long-term capital gains. Because it already tells me short-term or long-term, I will simply report the totals with acquisition and sell date(s) as “various”.

LendingClub 1099-B (Folio secondary market). If you sold any loans on the secondary Folio market, then the sales should be reported here. It should also be broken down into either short-term or long-term gains or losses. I will simply report the totals on Schedule D, using my acquisition and sell date(s) as “various”.

LendingClub 1099-MISC. I would just type this form into TurboTax box-by-box or submit directly to your accountant, usually under “Other Income”. Box 7 amounts will be subject to self-employment taxes, Box 3 amounts will not.

Prosper Lending

Prosper 1099-OID. Similar story to the LendingClub 1099-OID above, except they just give you the total from all your loans. Again, I have all zeros except for Box 1, which I will report as ordinary interest income on Schedule B.

Prosper 1099-B (Recoveries for Charge-offs). Again, anything listed here should be broken down into either short-term or long-term capital gains/losses and recorded on Schedule D. Prosper includes loan charge-offs on this form.

Prosper 1099-B (Folio secondary market). Again, anything listed here should also be broken down into either short-term or long-term gains or losses.

Prosper 1099-MISC. I would just type this form into TurboTax box-by-box or submit directly to your accountant, and it should be pretty straightforward. Box 7 amounts will be subject to self-employment taxes, Box 3 amounts will not.

*Reporting Charge-offs

If you have loans that were charged-off in 2013 (loan is very late and attempts to collect have failed, so they give up), you can write them off as a non-business bad debt. You can find these in either your year-end statements (LendingClub) or your 1099-B form (Prosper). These are all treated as short-term capital losses, which you can use to offset short-term capital gains from other investments or you can deduct against up to $3,000 in ordinary income per year (with the balance carrying forward to the next year).

More resources: Let me also recommend Peter Renton’s post at LendAcademy, the follow-up comments on that post, and this forum post by AmCap as good references for an intelligent discussion on the topic. Also see the LendingClub and Prosper tax pages, even though they aren’t especially helpful.

Tax Prep Guide 2013: TurboTax vs. TaxACT vs. H&R Block Online

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According to an informal 2012 poll, 86% of blog readers prepared their own taxes using software with a breakdown of 60% TurboTax, 21% TaxACT, and 16% H&R Block at Home. This nearly matches the findings of analytics firm Comscore, which found that of online filers 60% used TurboTax, 18% used TaxACT, and 15% used H&R Block at Home.

I’ve used all three programs over the years and each has their clear strengths and weaknesses. The NY Times recently did their own 3-way comparison with very similar experiences to my own. They actually called in for help and reported the results, so I’ve added this factor into my lightning review:

The major differentiating factors are price, time-saving features, audit support, and ability to answer specific tax questions. In terms of accuracy, I think all three are nearly identical. All three offer a “Maximum Refund Guarantee” (relative to competing software) as well as an “Accuracy Guarantee” (relative to your tax liability) that says that they will pay any penalty and interest assessed by the IRS or your state due to calculation errors on their part (though H&R Block limits this to $10,000). Actual cost can vary widely with sales and discounts, listed here are just the everyday prices.

tt180TurboTax Online

  • Most expensive. Federal Deluxe regular price is $29.99 w/ e-file. However, you now need Premier at $49.99 if you have an investment gains or losses. State return price is $36.99.
  • Best import support from payroll providers and financial institutions for automatic import of W-2 and 1099 forms. Works with free “ItsDeductible” program to help with recording charitable donations.
  • Moderate audit support (you get help, but no in-person representation)
  • Specific tax advice – Free online chat included. Did not provide definitive answer to NYT reporter’s question.

Bottom line: The time-saving choice if you have a lot of brokerage transactions, W-2s, or other 1099 forms to electronically import this year. Also if you have a lot of details to import from last year’s return with TurboTax. It may be worth the extra cost to avoid tedious data entry.

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  • Cheapest overall with Federal Deluxe regular price at $12.99 w/ e-file. Federal + State return combined including e-file at $17.99.
  • Limited import support (worst of the three).
  • Limited audit support (worst of the three).
  • Specific tax advice – Phone support only, online chat not available. Did not provide definitive answer to NYT reporter’s question.

Bottom line: The value choice if you just want accurate DIY tax return software and don’t need any extra assistance.

hr160H&R Block at Home Online

  • Middle-of-road pricing. Federal Deluxe regular price is $29.99, but includes investments. State return price is $36.99.
  • Moderate import support for 1099s and W-2 (not as broad at TurboTax, better than TaxACT)
  • Best free audit support. Only product that includes an H&R Block Enrolled Agent actually attending your audit in-person. However, consider whether you would hire your own representative in the actual event of an IRS audit.
  • Specific tax advice – Free online chat included, only one to provide definitive answer to NYT reporter’s question.

Bottom line: The got-your-back choice if you want the assurance that a federally-authorized enrolled agent will guide you for free through a potential albeit unlikely audit. Anecdotally the one most likely to provide answers if you have harder tax questions.

Free TurboTax Deluxe Online with State Farm Bank Account

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Works again for Tax Year 2013. State Farm is again offering their bank and credit card customers TurboTax tax-prep software at a significant discount. TurboTax Federal Deluxe Online is free, Premier is $20, Home & Business is $30, and State is also included free with e-File for all versions. Software downloads are also available (Deluxe $20, Premier $30, Home & Business $40). I ran an experiment last year and found it only took a one-time $25 deposit and a week’s time to obtain this valuable perk. Details below.

(Side note: TurboTax Deluxe 2013 no longer supports stock and mutual fund sales reported on Schedule D. You must now pay for the $20 Premier version in order to get this feature. Rather disappointing feature reduction, Intuit!)

According to my blog archives, from 2006-2009 State Farm offered TurboTax Deluxe for free to all customers including insurance policyholders. Starting in 2010 or 2011, they started offering it only to bank and credit card customers. I recommend opening a “Free Checking” bank account instead of a new credit card account, as many other credit cards are offering $500+ value in sign-up bonuses while the State Farm one does not. I’d much rather get $500 for a credit check and just put $25 in a State Farm bank account indefinitely while earning the same perks. Think of it as earning 50% APY interest every year on that $25! I did not get hit with a credit check for opening the State Farm bank account.

New Bank Account Application Process Details

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IRS Estimated Taxes Due Date Calendar 2013

Reminder for last quarter of 2013. If you’ll earn income outside of your W-2 paycheck this year, you may need to send the IRS some money before the usual tax-filing time. Here are the due dates for paying quarterly estimated taxes in 2013; they are supposed to be in four equal installments. This is for federal taxes only, state and local tax due dates may be different.

Tax Year / Quarter Due Date
2013 First Quarter April 15, 2013 (Monday)
2013 Second Quarter June 17, 2013 (Monday)
2013 Third Quarter September 16, 2013 (Monday)
2013 Fourth Quarter January 15, 2014* (Wednesday)

* You do not have to make the Q4 payment due January 15, 2014, if you file your 2013 tax return by January 31, 2014.

Who needs to pay estimated taxes?
In general, you must pay estimated tax for 2013 if both of the following apply:

  1. You expect to owe at least $1,000 in tax for 2013, after subtracting your withholding and credits.
  2. You expect your withholding and credits to be less than the smaller of
    • 90% of the tax to be shown on your 2013 tax return, or
    • 100% of the tax shown on your 2012 tax return. Your 2012 tax return must cover all 12 months.

If you forget to pay (like I’ve done before), then you should make a payment as soon as possible even though it is late. This will minimize any penalty assessed. This is all taken from IRS Form 1040-ES [pdf].

How do I pay?

  • By check. Fill out the appropriate 1040-ES voucher (last page) and send to the indicated address. If it is postmarked by the due date, the date of the U.S. postmark is considered the date of payment.
  • By online bank transfer. You can link your bank account and pay via electronic funds transfer at EFTPS.gov or call 1-800-555-4477. No convenience fees. It takes a little while to set up an online account, so plan ahead.
  • By debit or credit card. Here is page of IRS-approved payment processors. Pay by phone or online. Fees will apply.

I usually pay online at EFTPS.gov for both convenience and to avoid fees. In rare cases with the right credit card promotion, it can be worth it to pay the credit card processing fee. For example, last year I paid taxes with my Chase Ink Bold card. I paid $189 in fees, but earned $500 of bonus points.

TurboTax vs. TaxACT vs. H&R Block at Home: 2012 Lightning Review

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According to a MyMoneyBlog.com reader poll taken last year, 52% used TurboTax, 18% used TaxACT, and 14% used H&R Block at Home to prepare their tax returns, which agreed with the most popular software overall in the US. The remaining 16% either used an accountant (10%), filed on paper (4%), or used another software (2%).

Last year, I used each of “The Big 3″ to do my taxes in order to compare and contract in detail the three software programs. (As an example, my TurboTax 2011 review talks about comma-insertion as a feature…) I plan to do the same thing this year, but to help you early-birds, here’s the highly-condensed version of my reviews:

Accuracy and Maximum Refund Guarantees
In terms of accuracy and interview style, I think all three are comparable if not nearly identical. In fact, I’m certain they all dissect each other’s products annually to ensure this. As such, all three offer a “Maximum Refund Guarantee” as well as a “Accuracy Guarantee” that states that they will pay any penalty and interest assessed by the IRS or your state due to calculation errors on their part (though H&R Block limits this to $10,000).

In my opinion, the remaining major differentiating factors are price, time-saving features, and audit support. Now, there are various discounts and sales that pop up, but here I’m just comparing regular sticker prices.

TurboTax Online

  • The most popular and most polished-looking user interface.
  • Federal Deluxe regular price is $29.99. State return price is $36.99.
  • Best import support from payroll providers and financial institutions for automatic import of W-2 and 1099 forms.
  • Moderate audit support (you get help, but no in-person representation)

Bottom line: The time-saving choice if you have a lot of brokerage and/or bank 1099s to electronically import, or a lot of details to import from last year’s return and you used them last year. For those like me that would pay extra to avoid all that tax lot data entry.

TaxACT Online

  • Cheapest overall with Federal Deluxe regular price at $9.99. Many can get by with Federal Free version. Cheapest state return at $8.00.
  • Again, just as accurate as the others.
  • Limited import support (worst of the three).
  • Limited audit support (worst of the three).

Bottom line: The value choice if you just want reliable DIY tax return software and don’t need any extras.

H&R Block at Home Online

  • Federal Deluxe regular price is $29.95. State return price is $34.95.
  • Moderate import support for 1099s and W-2 (not as broad at TurboTax, better than TaxACT)
  • Best free audit support, as it includes an H&R Block Enrolled Agent actually attending your audit in-person. Neither TurboTax and TaxAct not offer representation. However, you must think about whether you would hire your own representative in the actual event of an IRS audit (probably depends on severity).

Bottom line: The sleep-well-at-night choice if you want the assurance that a federally-authorized enrolled agent will guide you for free through a potential albeit unlikely audit.

Free State Income Tax E-File Options For All 50 States

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Completely updated in 2013 for Tax Year 2012 returns. Whew, that took a while!

When shopping for tax prep software, always look at the total price including state return software and any additional charges for state e-file. For example, even the free version of TurboTax Online charges $27.99 for state returns with e-File, while other versions charge $36.99. If you buy the TurboTax Desktop version on Amazon with state software labeled “TurboTax Deluxe Federal + E-File + State 2012″, the state e-File is still an additional $20.

More and more states are offering their own in-house online income tax filing. This makes sense, as it reduces errors and saves the state from having to go through all those paper returns. Many other states have partnered with the “Free File Alliance” to offer free online filing for certain groups, usually limited-income households, senior citizens, young adults, and/or active duty military personnel. But again, read through the restrictions carefully and calculate the total price including Federal before committing.

As a baseline, remember that you can get both Federal and State tax prep including both free Federal and free State e-File from TaxACT.com for $14.95. See my lightning review of TaxACT, TurboTax, and H&R Block for why it may be worth it for some folks pay more for the time-saving or audit-protection features of the “brand name” products.

Below, you’ll find free e-file information for all 50 states. I found it interesting how some states have sleek websites and some still seem stuck in 1997. Be sure to read all the details, as you might have to click through a specific link to qualify.

In alphabetical order (just click on the state):

State Restrictions
Alabama Free through My Alabama Taxes (MAT). No major restrictions.
Alaska (no state income tax)
Arizona Various FreeFile options. Income and/or other restrictions apply, but free fillable free PDF forms for all.
Arkansas Various FreeFile options. Income and/or other restrictions apply.
California Free through CalFile. No capital gains/losses or Schedule C income allowed.

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2013 401k, 403b, 457, TSP Contribution Limit Increases – Historical Chart

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The IRS recently announced increased contribution limits for various qualified retirement plans for tax year 2013. The limitations are indexed to increases in cost-of-living (inflation) as per section 415 of the tax code. In particular, the elective deferral (contribution) limit for employees who participate in 401(k), 403(b), most 457 plans, and the federal government’s Thrift Savings Plan is increased from $17,000 to $17,500. However, the additional catch-up contribution allowed for those age 50 and higher remains $5,500.

The limits are the same for both Roth and “Traditional” pre-tax 401k plans, although the effective after-tax amounts can be quite different. Employer match contributions do not count towards the $17,000 elective deferral limit. (Although technically the total annual defined contribution limit is $51,000 for 2013… let me know if you have an employer that is so generous!) Curiously, some employer plans set their own limit on contributions. A former employer of mine had a 20% deferral limit, so if your income was $50,000 the most you could put away was $10,000 a year.

Here’s a historical chart and table of recent contribution limit increases:

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2013 IRA Contribution Limit Increases – Historical Chart

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The IRS recently announced the Traditional and Roth IRA contribution limits for tax year 2013. The limitations are indexed to inflation, but only in $500 increments (as of 2010) which are triggered when the cost-of-living calculation reaches a certain threshold. The threshold was finally met, so the limit on annual contributions to an Individual Retirement Arrangement (IRA) increases to $5,500, up from $5,000. However, the additional catch-up contribution allowed for those age 50 and higher remains $1,000.

The limits are the same for both Roth and Traditional IRAs, but each one has their own unique set of eligibility requirements. IRAs are “individual” accounts by definition, so the limits are per person. The deadline for 2012 tax year contributions is the same as the 2012 tax return filing deadline: Monday, April 15, 2013. Tax return extensions won’t apply to this cutoff.

Since I like visual aides, here’s a historical chart and table of recent contribution limits. I’m proud to say that we’ve both done the max since 2004. Have you been taking advantage of your potential IRA tax break?

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Your Job Search Expenses May Be Tax-Deductible

Help Wanted Sign; image credit: underbid.comHere’s a friendly reminder for those on the hunt for a new job. Many job-search expenses may be tax-deductible, so knowing the rules can save you money at tax time. As you might expect from the IRS, the rules aren’t straightforward:

  • You have to be looking for a new job in your present occupation, even if you never get one.
  • There cannot be a “substantial break” between the ending of your last job and your looking for a new one. Vague? Yep.
  • You cannot be looking for a job for the first time. Sorry, recent graduates.
  • Job search expenses are lumped in with many other “miscellaneous deductions”, such as the home-office deduction, union dues, work-related education expenses, bad business debt, tax prep fees. These are only deductible from your income if you itemize deductions and only to the extent that taken together they exceed 2% of your adjusted gross income. But if you’re out of work, 2% may not be a very high hurdle.
  • If you get reimbursed for any your expenses, then it’s no longer deductible. At least that one makes sense.

What qualifies as an expense?

  1. Employment and outplacement agency fees. This includes “career consultants” and the like. I don’t know if paying these are necessarily a good idea in the first place, but they can be deducted.
  2. Resume preparation costs.. You can deduct amounts you spend for preparing and mailing copies of your resume to prospective employers. These include paper, postage, envelopes, and printing/copying costs.
  3. Travel and transportation expenses. If you travel to an area to look for a new job in your present occupation, you may be able to deduct travel expenses to and from the area if the trip is “primarily” to look for a new job. In other words, you need to spend more time looking for work than doing any personal activities. Roundtrip airfare, car rental, and hotel stays can add up quickly. If you drive, you can deduct the standard mileage amount (55.5 cents per mile in 2012).

    Keep good records of your efforts and any meetings and/or interviews with prospective employers. Write down the time, date, and place of any event, and keep business cards and food receipts.

Things you can’t deduct include services like residential home phone service, cell phone plans, and high-speed internet.

This is all taken from the notoriously vague IRS Publication 529 – Miscellaneous Deductions. Look under Unreimbursed Employee Expenses > Job Search Expenses. Keeping great records for everything is key. If you have an accountant, be sure to ask them how to best take advantage of this area. Finally, if you do land a new job, don’t forget that you can also deduct moving expenses:

To qualify for the moving expense deduction, you must satisfy two tests. Under the first test, the “distance test”, your new workplace must be at least 50 miles farther from your old home than your old job location was from your old home. If you had no previous workplace, your new job location must be at least 50 miles from your old home.

Save More vs. Earn More: A Dollar Saved Is Two Dollars Earned

Earn more. Save more. Those are the two ways to get out of debt and build wealth. I’m a big proponent of doing both, but for many people it may be easier to cut back on some luxuries rather than land a higher-paying job, start a side business, or become an investing wizard. It’s also more effective due to marginal tax rates. Let’s say you are single resident of California and your (taxable) gross income is $50,000 a year.

If you were to go out and earn another dollar as an employee, here’s how that additional $1 would get broken down:

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You’d only keep 58 cents. On top of that, a lot of extra or freelance work is done as an independent contractor. That means you’re self-employed and get the happy task of paying another 7.65% of payroll taxes (the employer share), which brings your total tax hit to 49.6%! So in order to keep $1 in your pocket, you’d have to get someone to pay you $1.99. In that case, your choice becomes:

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This relationship helps me visualize the power of spending less. Now when you save $1, you can feel good knowing that you’d have to have earned $2 of income to equal that. But on the flip side, when I get a check from a side project for $500, I know I’ll only keep $250 of it. :(

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