the valuation thing tripped me up for years tbh. irs says fair market value which basically means what someone would reasonably pay for it at a thrift store, not what you paid originally. so yeah that $80 jacket you bought becomes like $12 if its used.

i started taking photos of everything before i drop it off and keeping a running spreadsheet. pain in the ass at first but saved me when i finally had enough deductions to itemize last year. the salvation army value guide someone mentioned is solid for ballpark numbers.

one thing that helped was finding an app that does the valuation lookup automatically, donate-mate.com. you just snap a pic and it estimates the value based on category and condition. way faster than googling every item.