A very close friend of mine has been recently (the last few years) using a strategy of clothing donation to maximize his tax write-offs. I don't think he is wrong in what he does, but from what I gather it could still be a red flag and I wanted to get some more opinions before I follow suit!
If you can feel comfortable donating to the Salvation Army or Goodwill, then you can write off up to 50% of adjusted gross income. The trick he uses is that he will go to garage sales, rummage sales, and other events where you can get very cheap clothing (also other goods, but he focuses on clothing) - and in no time at all he can 'invest' a great deal into buying tax credits.
The key he uses is to be as cheap as possible. He will literally go pick up gently used stuff that can be as little as 4 t-shirts for a quarter. Total invested would only be $1.00 for the four shirts. Then, if you go look at the Salvation Army donation schedule (just one place to donate at)
https://satruck.org/Home/DonationValueGuide .... you can see there is a value on Men's shirts between $2.50 and $12.00 apiece. In other words, he spent $1.00 (plus time and energy to get there of course), and in return will be able to receive back $10 to $48 in donations. Not to mention he doesn't just go and pick up 4 shirts ... he will go and grab 50 or 100 if possible. The best part is, he isn't looking for size, just cheap clothes. So he can grab men's, women's, and even children's clothing. Put it into bags when he buys it... never even take it home ... drive straight to salvation army and drop it off for tax credits.
Here's my question. While I know you need to itemize to write off charitable contributions ... are there any red flags he should keep in mind (or that I should be aware of if I were to use this strategy)?
Also, is he forgetting something, or for an individual who makes slightly over 70k a year, is he really writing off 35k right off of the bat and not being taxed on half of his income?
Because again, in order to generate that 35k of donations ... it wouldn't be THAT hard. If he could sustain making as much as $5.00 per T-shirt (which means he donates it at 5.25 if he purchases it for $.25 .... right in the middle of the $2.50-$12.00 spectrum), then you would STILL need 7,000 t-shirts. While that is very ambitious ... it's not unheard of. Going to a neighborhood where there is a block sale, going to a flea market, or doing something along that mindset would easily net countless shirts. Especially when you aren't even limited to Shirts AND you aren't even worried about the design or fashion - just quality of clothing.
Throw in the fact that you would be saving roughly $7,000 in the process (the taxes on the last $35,000 that would have been written off for a person in the 70k salary range ... which is 20% rate). And, while it is absolutely not a home run, you could pocket (or keep from paying in taxes) almost $7,000 just by taking a handful of Saturday mornings and filling up your van with old clothes and chauffering them all down to the Goodwill or Sal-Val!
Again - I think it works, but for meaningless work I also think it could be too good to be flawless...