If you are a homeowner, are self-employed or were hit hard with medical bills last year, it is almost always worth your while to itemize your deductions when filing taxes this April. Remember, you may be able to deduct expenses for the following items:

* charitable contributions
* owning a clean-fuel vehicle
* disaster relief contributions
* prescription medicinces
* stop-smoking programs
* travel and transportation expenses
* alimony

The rule of thumb on whether to itemize is simple: can you deduct more in mortgage interest, charitable contributions, state taxes, than the standard deduction? — $10,000 for married couples filing jointly and $5,000 for a single filer. Itemizing does take a little preplanning and organization in saving receipts and other paperwork documenting your expenditures.

If you are scrambling to retrieve those important papers that may be scattered hither and yon, consider investing in a spreadsheet, such as Quicken or Microsoft Money. Even if you aren’t tackling your own taxes this year, you could slash your tax-preparation fee in half. Microsoft.com says Microsoft Money 2006 can “eliminate the paper chase, allowing you to sort out important tax information from day-to-day expenses, make educated tax investments and minimize capital gains taxes.” Microsoft.com also recommends doing a little research on the front end to find out what can be deductible. The website suggests checking out MSN Money to “learn about contributing to funds like IRA’s, ESPs, and OTPs, which may be tax deductible.”

Here are a few deductions that www.msnbc.msn.com recommends you remember:

* Charitable contributions. If your donations are $250 or less, you do not need to include receipts. Any amount over that, however needs to be documented. According to the website, generally you can’t contribute more than 50 percent of your adjusted gross income, but under the Katrina Emergency Tax Relief Act of 2005, you can waive that restrictions for donations between Aug. 28 and Dec. 31. In addition, the IRS says you can also use a higher standard mileage rate and exclude mileage reimbursements from income.
* Education expenses that can range from saving for your kid’s college to paying off your own student loans.
* Home-office expenses if you work at home.
* Medical expenses if they exceed more than 7.5 percent of your adjusted gross income
* Miscellaneous deductions. According to the IRS, these can include depreciation on computers or cell phones, job search expenses, hobby expenses, military uniforms, safe deposit box rent, gambling losses, trustee’s administrative fees for IRA.

With a little research and organization, you can end up saving a lot of money by itemizing deductions. So throw away that shoebox you’ve used to store receipts. Its never too early to get organized.