[twoodfin]

Yes, there are lots of “loopholes” available if you are willing to commit tax fraud! But that’s something anyone can do, it’s not particularly harder to lie about the value of charitable donations if you’re not ultra-wealthy.

[loloquwowndueo]

Loopholes are by definition legal.

[twoodfin]

Bribing an appraiser to get a larger deduction on a donation is cut-and-dried tax fraud. It’s not a “loophole”.

[loloquwowndueo]

Correct. Fraud is fraud, loopholes are loopholes. One is legal, the other is not.

Or put another way - a loophole in law/regulations is found, then the law/regulation gets changed to close the loophole. If it were not legal this change would not be necessary - you would just prosecute.