Is it worth the trouble non cash deductions?

[Green Tea]

If Goodwill gives a generic receipt, isn't the IRS just taking your word for what you say you donate? You could write down anything that way. I thought you had to have original clothing receipts?

For an item of clothing, the new cost is irrelevant. The only value that matters is its used value to the charity.

Yes, people can and do write anything down....it is called tax fraud. Just keep a record of what you donated, then you have a backup to supplement what was in the 6 bags written on the generic goodwill receipt. It isn't fraud to donate, it is allowed and good for both you and the charity.

 

[Green Tea]

I spent some time looking around this year and apparently if you donate more than $500 worth of stuff in a category you are supposed to have original receipts. Nobody actually does, but I'm a little pissed that I unloaded my entire closet right at the end of the year. I took over a couple hundred maternity items and about 400 shirts and pairs of pants that didn't fit one of us right. I don't have original receipts for any of it but I had my entire wardrobe from before DD, the wardrobe from before DS and the wardrobe from before this pregnancy!
The goodwill store will probably make $2-3,000 from my clothes and I'm nervous to claim more than $500.

I also completely filled my mini van with old furniture and toys twice. I had a good few weeks of destashing.

I really don't think it is per category. I think it is on individual items of high vale-then you need an appraisal, receipt, other documentation.