Yeah the bigger concern with tax write-offs for donations is that it allows the wealthy to refuse to pay for what has been democratically decided on and instead put it towards what they want

There’s no amount of writeoff that makes donation profitable, compared to simply keeping the money. The exception is when the rich “donate” to “charities” that they then use for their personal benefit. Then they get a writeoff AND full control of the money.

I mean, kind of? Usually you're donating to a charity or something to minimize your tax burden or claim a loss.

"Profitable" is kind of a relative term, but if I pay a little bit of nothing for a good stock (for example) and I hold it for a long time, I might have to pay capital gains on like 90 percent of the value of a stock. If I have some more recently purchased stock with a out the same value, what I can do is donate my old stock money that super grew tax free and use it to offset the value of selling a LOT of more recent stock. This puts money in my pocket from the market basically for free.

It is definitely profitable to figure out how to get money from the market that doesn't require you to pay a quarter of it in taxes up front. If the weight is "how much I put in" vs "how much I took out" you can definitely make profitable tax write-offs.