A poet once wrote that April is the cruelest month, and who knows? He might have been motivated to write that line as he filed his income tax return for the previous year.

It’s nobody’s favorite activity – but before you know it, that familiar 1040 time will be here again. Right now is the time to begin lining up those legitimate deductions that will reduce the amount you’ll owe Uncle Sam. In fact, now is also the time to look ahead and begin planning for 2009. In the meantime, don’t forget to consider write-offs that can easily be overlooked, such as these:

Charity begins with a tax deduction. Did you donate clothes, furniture, or other items to a charity such as Goodwill during the previous year? If so, the value of those items is deductible. Just be sure you have a written receipt as proof should you happen to get audited. You’re also entitled to a deduction if you dumped old (but serviceable) clothes into a Salvation Army box; unfortunately, that kind of charitable contribution doesn’t come with a receipt. In the immortal words of Clint Eastwood’s Dirty Harry, “Do you feel lucky?”

Put a premium on health insurance deductions. Your health insurance premiums, as well as certain long-term care premiums, might be deductible. Remember, though, that your total medical expenses must exceed 7.5% of your adjusted gross income (AGI). If, however, you’re self-employed and not covered by another employer’s plan, you can deduct 100% of your health insurance expenses because they’re included in your AGI – meaning that they don’t have to exceed that 7.5% figure. In fact, they don’t have to be itemized at all.

Remember tax planning and investment expenses. It’s easy to forget those expenses because they fall into the category of miscellaneous itemized expenses. Some to keep in mind are employee business expenses, tax preparation fees, and any portion of your legal or accounting fees having to do with tax planning. As for investment expenses, don’t overlook the annual fee paid your broker or any IRA fees. Also, while you’re compiling your long-distance phone calls to your broker and investment adviser, don’t forget that the mileage to visit them is also deductible.

Take retirement into account. Contributions into your retirement account aren’t taxed until you begin withdrawals. In the meantime, those contributions are a deduction from your taxable income. What’s more, you’re entitled to a credit of up to 50% of the first $2,000 you invest – a reduction of as much as $1,000 off your tax bill.

These are only a few of the more common items you’ll want to take into consideration when preparing your return. There are plenty of others, so be sure to thoroughly discuss all potential deductions with your tax advisor. The whole idea is to make your April a kinder, gentler month.

Related Posts:

1. Why Tax Preparers Find Extra Deductions on Your Return
2. Turn Your Donations Into Tax Deductions
3. 7 Little Known Tax Write Offs
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5. Health insurance