Ask a CPA

Generally points are deductible in full in the year paid if 6 requirements are met. Form 1098 Mortgage interest statement is used to report the amount of the paid points. Points paid to refinance an existing mortgage must be amortized over the life of the loan unless the loan proceeds are used to substantially improve the main residence. The portion used to improve the residence can be deducted in full in the year paid. Speak to your local CPA about the 6 requirements.

No. Rent payments are not deductible for Federal purposes. Some states allow a deduction or credit for rent paid. Speak to your local CPA for a possible deduction or credit on your state tax return.

Generally, Yes. Timeshares can be considered second homes for mortgage interest deductions. Most timeshares can take advantage of the mortgage interest rules depending on the type of timeshare it is. Speak to your local CPA to determine the classification of the timeshare such as either a "fee simple" or "deeded" or "right to use" timeshare. This classification will determine its deductibility.

When certain criteria are met, Interest on a boat loan are deductible as a second home subject to the mortgage interest rules.
The boat must have basic living accomodations, such as toilet facilities, sleeping space and cooking facilities.

NO. Only the mortgage interest and real estate taxes paid at the closing are deductible in the year paid. The other costs at closing are added to your cost basis of the residence (and improvements over the years) to be used when you sell the residence to determine if there is a gain or loss on the sale.

For contributions of $250 or less, a cancelled check or credit card statement is sufficient.
For contributions of $250 or more, you must have written substantiation from the organization. A cancelled check is not sufficient.

Usually you can use the average (poor, average, perfect condition)fair market value method.
Speak to your local CPA. He/She usually has checklist from a recognized IRS charity such as the Salvation Army with recommended non-cash (clothing) contribution deduction amounts.
When the value of this donation is more than $500, IRS Form 8283 is required to be filled out.

A casualty or theft loss can be deducted if it is a qualified casualty and the total amount of the loss, minus $100, is more than 10% of your Adjusted Gross Income. Speak to your local CPA about the loss and for his help preparing IRS Form 4684

Yes. You must report the total amount of your gambling winnings from Form W-2G as miscellaneous income on IRS Form 1040 page 1. However, you are allowed to deduct gambling losses up to the amount of the winnings as another itemized deduction on IRS Schedule A.

The costs of buying and maintaining clothing that can be considered suitable for street wear are not deductible.
The costs of buying and maintaining Uniforms or work clothes not suitable for street wear are deductible. Uniforms for police or fireman are examples of uniform itemized deductions.