5. Losing track of receiptsIn the real world, you either have proof of your deductions or you lose them. Always keep your receipts and checks if you want to deduct them. Deductible receipts and checks should always be kept for at least three years from the due date of the year filed, or the actual date filed, if later. Unless the IRS can prove fraud, the statute of limitations to disallow deductions is three years. Once this three-year period has elapsed, the IRS is prohibited from even questioning these deductions. Receipts for expenses that may be deducted in later years, such as improvements to your house, should be kept for three years after the return on which they are claimed.Remember, the IRS is a paper-based bureaucracy. Separate your receipts and checks by deductible category and make any audit easier for the auditor. The easier you make it for them, the more they believe and accept that you know what you are doing, and the easier they will make it on you.6. Failing to bunch deductionsThere are a number of deductions that are allowed only after you exceed a minimum amount. For example, only those medical expenses that exceed 7.5% of your adjusted gross income are allowed. Alternatively, miscellaneous deductions are allowed only to the extent that they exceed 2% of your adjusted gross income.Your best planning strategy here is to bunch your deductions into a single year to exceed these minimum requirements. For example, if you have an adjusted gross income of $100,000, only those medical expenses in excess of $7,500 can be deducted. In order to exceed this "floor" amount, you might prepay your orthodontia bill or pay your Jan. 1 medical insurance on Dec. 31. With miscellaneous itemized deductions, and the same adjusted gross income, you need to exceed $2,000 in expenses. Prepay your tax preparer on Dec. 31 for that year’s taxes or bunch order your investment subscriptions and expenses to exceed that amount.7. Forgetting to donate unwanted items to charity before Dec. 31Give your old clothes, furniture, appliances and other items away to your favorite charity. The wholesale value of those contributions is allowable as a charitable deduction. Make sure that you get a receipt. No receipt, no deduction. The receipt doesn’t have to list what you gave or what the items were worth, but it must be dated. You can fill in the details yourself. Remember, too, that you can deduct 14 cents a mile for any charitable work, including the trips to bring the old clothes to the charity.