I am getting ready to do a thorough cleaning of my house, which will include many donations to Good Will. In the past when I have done my taxes (using the H&R block online) the maximum non-cash donation they allow is $500 without having to do additional paperwork (which seems complex), and the receipts that I get from my donations aren't that thorough. For example, if I donate a bag of clothes the receipt will say 'clothes.' It doesn't give a thorough explanation of what clothes were donated (like 2-suits, 3-sweaters, etc.).
Does anyone have experience or know the best way to document non-cash donations that will allow me to take the maximum donation I can?
In this cleaning that I plan on doing there will be a lot of clothes from the household, furniture, kitchen electronics, and other things that I find in my house that someone else could use. Should I get appraisals? Take pictures? write down details of the information?
Also, what is the best way to claim these donations with taxes (for 2008)? Would a good online tax program let me take larger donation?