He made $500+ in tips alone yesterday (200 for star wars and 300 from pokemon), that on-top of patreon, ad-revenue from YT and Twitch (thosuands of dollars of double dip free money a month) and Twitch sub payments means he makes more than enough to offset some game costs up-front. Keep in mind he splits his tips goal up during the day and starts from $0 again on the "late stream" to fool people into thinking he has been given less than he actually has that day. Also video games and anything else he buys (including stupid outfits, electricity costs etc) for his self employed "business" are a work expense by tax law, so are tax deductions anyway. He effectively gets anything that's for his job for free (upto a certain limit obviously, $12k a year or so i think when married, which is why he got married in the first place...greater tax benefits).
Whether you think streaming is a dumb job or not is irrelevant to the tax office, it's still the persons lawful job and work expenses for games are classed the same as a carpenter buying tools for his business. Since there is a cap on deductions he still wants some "gifts" obviously though.
However buying as many games as possible (that he can play without getting swamped) makes good business sense since new games lure bigger tips and they are tax deductions anyway, he would be dumb not to buy a lot of big games.
You've probably heard the phrase "tax deductions" a hundred times. But what does it mean? And how can you be sure you're taking all the tax deductions you're entitled to?
money.howstuffworks.com
He is making a lot of money doing what he does right now, way way more than he would ever get doing anything else ever. His problem is that he was working as a self employed youtuber at the start, making a lot of money and just didn't bother paying any taxes on any of it cause he was a dumbass. So he owed a lot of back taxes when they found out, once those are paid off he will fine. He won't tell anyone when that happens of course, why would he say when he has a good racket going on. For all we know he has already paid off his back taxes and other issues long ago and is just playing the gig now. There will never be a time when he says "My taxes and bills are all paid now, thanks everyone!", he would be insane to say that ever because he knows this works for him to get more money.
He will be 70 years old and still complaing about muh bills and new games costs if it still works for him.