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8 Tax Strategies to Consider Before 2010

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Photo: Mike Fillion

With only two weeks left in 2009, you might think that it’s time to throw
in the towel on your 2009 taxes. Not so fast! This is the prime time of year
to implement some smart tax deduction strategies. With minimal effort, you
can still have a huge impact on your 2009 tax return by decreasing your
realized income. If any of these strategies appeal to you, speak with a tax
adviser, pronto.

Strategy #1: Fund your Retirement:

You may still be able to add more contributions for your 401k in 2009.

Additionally, you will be able to make tax deductible contributions to a traditional IRA up until the 2009 tax filing deadline (April 15, 2010) for the 2009 tax year. The IRS maximum allowed 401k limit is $16,500 in both 2009 and 2010. For those 50 and over, the catch-up contribution brings you up to $22,000 both years. For IRA’s, the limit is set at $5,000, while the catch-up is $1,000 for both years. Check with your employer ASAP to see if it’s not too late to kick up your contributions.

Strategy #2: Hold Off on the Roth IRA Conversion:

Owners of traditional IRAs can convert all or a part of their accounts to a Roth IRA if their 2009 modified adjusted gross income is under $100,000.

Any amount converted is taxable income, but is thereafter eligible for the
potential tax-free distribution rules of Roth IRA’s. The big news is that
starting in 2010, the $100,000 income threshold is removed – anyone can do a conversion. For 2010 only, you also have the option to spread the income from conversion over the following two years (2011 and 2012). Many have been waiting for this opportunity.

Strategy #3: Sell Losing Investments (and Big Winners):

The S&P 500 index went from the low 900′s to a low of 666 (funny number,
right?) in March, back up to a 2009 high of 1,119. That’s one heck of a
volatile year. All in all, the market is up over 22% for the year. Depending
on when you’ve bought and sold, you might want to consider unloading big
winners to offset your losers, or big losers to offset your winners. First,
you must subtract your losses from any capital gains you’ve made. Next,
additional losses can offset up to $3,000 of your 2009 ordinary income.

Have larger net losses than $3,000? Losses above and beyond what you used to
offset your capital gains and ordinary income can be carried over into
future tax years. Before implementing investment loss strategy by selling
mutual funds, make sure that you won’t incur any penalty for holding shares
for too short of a period of time.

Strategy #4: Capital Gains Tax Cuts:

Under the Tax Increase Prevention and Reconciliation Act (TIPRA) of 2005,
US taxpayers in the two lowest tax brackets (10% and 15%) will pay no
capital gains taxes on long-term investments sold in 2009 and 2010.
Long-term capital gains result from profit made via appreciation of a
security (stock, fund, etc.) held for more than one year.

Strategy #5: When you Donate to a 501(c)(3), Everyone Wins:

Tax deductions for charitable donations can be claimed for the year in which
the donation is made. Perhaps it’s time to rummage through your house to
find valuables you no longer need or want that others can gain value from.
You may obtain fair market value on these items. Or, simply open your
checkbook or donate cash.

Donations of $250 or more must come with a written receipt or letter from
the 501(c)(3). When submitting your donation, ask for and keep all of the
appropriate documentation and receipts associated with all donations so that
you are safe in the event of a possible future tax audit. If you are
donating goods, document a description of everything given.

Strategy #6: Prepay your January, 2010 Mortgage:

If you’re a homeowner, you may want to consider making your January mortgage
payment in December, which will give you one more month of interest to
deduct from your 2009 taxes. Check with your mortgage provider to see if an
early payment is possible. It may be a great way to offset extra income
windfalls in 2009.

Strategy #7: Get Healthy on your Medical Bills:

If you have have large and predictable medical and/or dental bills that need
to be paid, consider making all the payments before the year is over. The
IRS allows families to itemize and deduct medical and dental expenses that
exceed 7.5% of their adjusted gross income, so if you’re close to going over
that percentage it may be wise to pay the bills to be able to make the
tax deduction.

It won’t affect your 2009 taxes (since it was already deducted), but don’t
forget to use up the rest of your 2009 FSA funds if you are in danger of
losing them in the new year.

Strategy #8: Prepare for 2010:

Using Mint.com to classify all of your deductible expenses in 2010, can allow
you to tag anything as tax related. Download your transactions to a
spreadsheet and send it to your accountant. If you’re doing your own taxes,
this info will give you a big head start in using online tax software, such
as TurboTax, which offers federal
filing free. If you expect that you’re due a hefty refund, file asap, so
that you can get back your return and re-invest it. Also, speak with your
employer about your withholding taxes if you have found that you owe too
much taxes or are getting a large refund.

Using TurboTax’s TaxCaster can help you estimate your tax burden and see the impact of any last-minute deductions.

For more of GE Miller’s writing, visit personal finance blog
20somethingfinance.com.

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25 Comments so far

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  1. GE,

    Your year-end tax strategies are great. We should all be thinking about our tax liability long before April 14th.

    I do have a few comments on 2 of your strategies:

    Strategy #2-Roth conversion.

    I’m not so sure this is a good strategy for folks in the $100k plus income bracket because:
    1) Why pay taxes today if you can put it off to tomorrow when (presumably) the dollar will be weaker and (hopefully) the tax code might be more favorable? Which leads me to…
    2) The government rarely enacts favorable tax laws just because they want to do you a favor. There’s a big hole in the federal budget and Washington is trying to plug it. Allowing these conversions will create an influx of taxes over the next 2 years which is good for the government’s balance sheet but is it good for yours?

    Strategy #6-Prepay your mortgage

    Thanks to a distracted Congress, we still don’t know what the final 2010 tax code will look like but one thing we do know…taxes are going up (see big budget deficit referenced above.) Because of this, you should shift income into 2009 and push expenses to 2010. Better the devil you know…

    Merry Christmas and many happy (tax) returns

    • Anonymous

      Betty,

      The reason you want to do #2 (pay taxes today) is because of your comment for #6 (taxes are going up). Especially for the 100,000k plus people, the Bush/Cheney tax cuts are soon to expire.

  2. #6 is a good one! I always try to front load business expenses when possible but I hadn’t even thought of paying my January mortgage payment early.

  3. Just remember! If you want to contribute to charitable organizations and use it on your 2009 tax return, you MUST itemize your deductions. You cannot claim donations with standard deductions. A lot of people do not realize this.

    See more: http://www.irs.gov/newsroom/article/0,,id=105101,00.html .

  4. Robert

    This is basic stuff. The real tax savings come from starting a business. If you really want to “prepare for 2010″, look into starting a business and hiring your kids. Businesses get the best tax advantages and anyone can start one. Consult an accountant to make sure everything is on the up and up though.

    • Robert, You are so right on this one. I think people get so caught up in the small things that will help, but I think one of the best things they can do is to start a business.

  5. Thanks for the great tips!
    I have a year-end tax question in regards to my student loans. I have been working for about six months full time and also going to school full time, and will likely be in a low tax bracket (~$35,000) for 2009. I do not need to make any student loan (Stafford) payments until May 2010; however I understand that any payments I make before then will go towards my interest, which is about $1,500.
    So my question is, would I be better off making a large loan payment before the end of 2009, and also is student loan interest deductible outside of the standard deduction? Or would I benefit more next year when my taxable income will be much higher, between $75-100k (and may itemize). I appreciate any help!

    • There is an income cap on deducting student loan interest. I believe it is $70,000, so if you will make more than that next year you will not be eligible to deduct your interest.

    • Yes EAA, student loan interest is deductible outside of the standard deduction – you do not have to itemize to deduct student loan interest.

    • Jordan

      Student loan interest is an above-the-line deduction, so yes, you can deduct it even if you don’t itemize. Definitely try to pay as much of your accrued interest as you can in 2009, since as green mentioned, you’ll likely be earning too much in 2010 to be eligible to deduct it.

    • someone

      Pay off your student loan interest this year and take deduction. I think you should be able to take deduction for the entire interest amount. As one other poster rightly said, you will not be able to deduct it once your income is higher.

  6. Thanks for the great tips on holding off on the Roth IRA Conversion, that saved me from making a big mistake.

  7. Something easier than starting your own business and hiring your kids?! is to look into home office deductions. Check with your accountant on how many hours are required to start deducting home office expenses included your rent! and utilities. More and more companies are pushing employees to work remotely. You can save a ton on your taxes if you qualify.

  8. With all respect, the delay the Roth advice is very simplistic. Look into the Roth conversion for sure, but why delay it? Not just because next year you get to spread paying the tax over two years. What happens if the tax rates are increased in the second year? If you did 1/rd now and 2/3rds next year, you’ll spread the taxes over three years with 2/rds in years where the tax is likely to be less than in year 3.

    Also Roth conversions make sense if you can pay from funds not in your IRA. Otherwise, its iffy at best.
    Moreover, to whoever said delay making the Roth conversion because taxes might go down: I have two bridges for sale, one in Brooklyn and one at the entrance to San Franciso Bay.

    There are a lot of things to consider before deciding to make or not make a Roth conversion, not the least of which is the tax position you will be in after making a conversion, and when you expect to take money out of a Roth/IRA.

  9. narasinha

    I have used the following excel worksheet at least to estimate my taxes for the past 4 years. It works out very well and you can try different scenarios
    http://home.mchsi.com/~taxcalculator/
    The tax form for 2009 wont be available till Jan 2010 however in the meantime one can use the 2008 tax form to get an estimate.

  10. willofcc

    Roth Conversion Comments – i quickly glanced the comments from the Roth tip; Betty asked why should she convert from a traditional IRA to a Roth IRA….because your money will grow tax free…let’s assume your IRA grows from $1 to $100. when you start taking distributions you’ll have to pay tax on that $100, it’s considered income…whereas in a Roth it’s treated like a checking account – no tax filing. a major major savings in time.

  11. Another tax idea is to donate to a 529 to fund a child or grandchild’s education. This is then a credit towards your state income tax/ That is true for Virgina but I am not sure for every state.
    Dick

  12. Could someone provide some advice on the non-typical child care expenses that are deductible. I bought my in-laws over from another country primarily for the purpose of looking after our toddler so that both my wife and I could go to school and work. Would the plane fair be deductible? How about any other expenses incurred?

  13. Note, that you can also gift appreciated securities to 501c3′s. If you have stocks, that have appreciated significantly in value, you can gift these and not get hit by the capital gains tax, and you still get the full deduction.

    Below, I am re-posting Facebook Users note about needing to itemize deductions to take the charitable deduction.

    —-

    Just remember! If you want to contribute to charitable organizations and use it on your 2009 tax return, you MUST itemize your deductions. You cannot claim donations with standard deductions. A lot of people do not realize this.
    See more: http://www.irs.gov/newsroom/article/0,,id=105101,00.html .

  14. Under your Roth suggestion, you MEANT to say the TAX can be paid over 2-3 years, not the income. I hope.

  15. Great Tips! Thank you for your research and thoughtfulness when it comes to helping people save money.

    Merry Christmas!

  16. KyCats

    Be careful with #3 and #4. If you are eligible for the zero capital gains tax rate, then your capital losses will be worth the same– zero. Also, your FEDERAL tax on capital gains will be zero (if you qualify) but STATE capital gains taxes probably still apply.

  17. Great information! I think I know it all every year, but don’t prepare the way I should until it’s to late. This is going to be different as I am going to be more prepared for tax time. Thanks!

  18. Rick Roloff

    In regards to the Roth conversion, and “why pay taxes now when you can wait”.
    We are in a historically low tax rates right now (not lowest ever but low in comparison to most of the last century). With baby boomers retiring, the work force is getting smaller, and on average people are making less money then the previous generation for the first time in american history. Factor in that the large number of people retiring over the next 10 to 15 years will be getting social security benefits from the government.

    Less people paying taxes, making less money (so in a lower tax bracket), more money going out in government aid…

    Government can borrow more (please no!), cut benefits (maybe a little but not excessively as senior citizens are highest voter turnout), or raise taxes.

    My money is on raising taxes over the next couple decades.

    So in my humble opinion, that is why you would want to pay taxes now instead of waiting!

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