great question
on the donation side the collective wisdom here on tug is: if you cant sell it, it must be worthless, so your donation to charity is a donation of $0
I think similar logic applies to a purchase from a charity
Heres an example: If you attend a charity dinner and the cost is $500, you cant deduct the entire $500 because you received something of value for your money....$500 less the value of the dinner ought to be an allowed deduction
using the same logic to the purchase of a timeshare from a charity...If you paid more than the timeshare is worth than maybe you have a deduction....But you probably paid exactly what its worth....so you received a dollars value for each dollar you spent, therefore no deduction
Please understand...Im not a CPA or Tax Attorney, so check what Im saying with someone that knows what they are talking about...My usual approach is; if I can make a reasonable argument for my deduction I do it and "when in doubt deduct" Some times i get away with it, sometimes not; but no jail time yet. and both times I was audited for real estate income and expenses, my return was accepted as filed