FYI, the answers to many of your questions are available by doing a Google search, but, as a start, here’s some info (below) from NOLO–generally a good source for this type of information.
I hope this is helpful, but please do not consider this advice, and you may want to contact a tax professional.
Tax Deductions for Charitable Contributions
You can deduct charitable contributions from your taxable income–if you follow IRS rules.
NOLO
When you make a charitable contribution, you benefit both the charity and your own tax situation, because you can deduct the amount of these gifts from your taxable income if you itemize your deductions. However, the IRS has lots of rules about how you must report and document all your charitable deductions. If you don’t follow the rules, you won’t get the deduction.
Cash Contributions
Claiming a charitable deduction is simple when you write a check to a charity or make an online donation with your credit card.
For a cash gift of any amount, you need a receipt (showing the date and amount of your donation) OR a bank or credit card statement, payroll deduction record, cancelled check, or other bank record showing the transaction. Email communications are generally acceptable. If you donate through a text message, the IRS will accept the phone bill as verification if it shows the recipient organization, the amount, and the date given.
If you want to claim a deduction for a cash gift of $250 or more, you must have a written receipt, describing the gift, from the charity. To determine whether or not this requirement applies to you, you do not have to add up all your donations to a particular charity. For example, if you give the local food bank $50 every month, each contribution is separate, and the receipt rule does not apply.
The receipt should also state whether or not the charity gave you any goods or services in exchange for your gift; if so, the receipt must describe them and give an estimate of their value. The charity doesn’t have to report a low-cost item it gives to you as a token of thanks—for example, a plastic water bottle or coffee mug with the charity’s name on it. You must get the receipt by the time you file your tax return.
Noncash Contributions
Making “noncash contributions”—in other words, donating clothing, books, cars, or other items—requires more documentation and sometimes a special IRS form. It all depends on the value of your gifts.
To figure out the value of your gifts, add all the value of all similar items. For example, if you give away a hundred valuable old books, add their value together even though you might think you’re really making a lot of small gifts. The rule applies even if you give the items to different charities.
Gifts of Less Than $250
To deduct a noncash donation worth less than $250, you need a receipt with:
the charitable organization’s name
the date and location of the contribution, and
a description of the property (in just enough detail to identify the items).
Clothing and Household Items. Most of us, from time to time, pass on clothing, furniture, appliances, and similar household items to charities, hoping others can use them. A tax deduction isn’t the main goal, but you can claim a deduction for these items, just like more valuable ones. The items must, however, be in good condition; you don’t get a deduction for giving a charity items that really should be thrown out. You can get values for commonly donated items from various commercial software programs or at the Salvation Army’s online Valuation Guide.
Gifts of More Than $250
If you want to claim a deduction for a gift worth $250 or more, get a written receipt from the charity that describes the gift. The receipt should state whether or not any goods or services were given to you in exchange for your gift; if they were, the receipt must describe them and give an estimate of their value. The charity doesn’t have to report a low-cost item it gives to you as a token of thanks—for example, a plastic water bottle or coffee mug with the charity’s name on it.
Gifts of More Than $500
If you make a total of more than $500 worth of noncash gifts in a calendar year, you must file Form 8283, Noncash Charitable Contributions, with your income tax return.
You have to fill out only Section A of the form if:
the gifts are worth less than $5,000, or
you’re giving publicly traded securities (even if they’re worth more than $5,000).
Special Rules for Donating Vehicles
Many charities actively solicit the donation of used cars and other vehicles. To claim a deduction of $500 or more for a vehicle you donate, you of course need a written receipt from the charity, issued at the time you make the gift or shortly thereafter.
How large a donation you can claim depends on what the charity does with the vehicle. If it promptly sells the car without using it or substantially fixing it up, you can deduct the amount the charity receives for the car or its fair market value when you donated it, whichever is less. If the charity does use or improve the car (or gives it away as part of its charitable activities), you can deduct the fair market value at the time of the contribution. The charity typically provides this information on IRS Form 1098-C, Contributions of Motor Vehicles, Boats and Airplanes.
