As a degenerate gambler myself I recently stumbled upon videos on youtube and have watched his last streams. As most of you I find it hilarious to see him tilt.
As I'm playing on stake.com, I can answer some gambling related stuff. Dice and Limbo for example are pretty much the same games, they just look different. You can set a multiplier and the chance of hitting the multiplier is slighty worse than the multi. The RTP (Return to Player) for the originals like Limbo, Dice and Keno is 99%, which is significantly better than slots (they are mostly in the 94-97% range). The highest multi you can set for dice is 9900x (you can choose if you want to bet on the under numbers or over. For 9900x you have to hit exactly the number 0.00 or 100.00). For Limbo, the max multiplier is 1.000.000x.
Regarding his income, he seems to get paid $1,750 per week by stake and his Kick subs are at ~1600, which equals $7600. The weekly and monthly is not part of his deal, every player gets a weekly every saturday at 12:30 GMT. Monthly is once per month but they drop it whenever they want, there is no fixed date. Both weekly and monthly amount depend on your gameplay, meaning your loss/win and your wager.
The way he's "desensitized" betting large like the $2000 dice rolls or $500-$1k Keno bets (utterly ridiculous), I think there is no almost no chance of him cashing out money and not gambling it away in minutes.
Regarding Stake I can say that they are definitely legit and don't ask questions when it comes to withdrawals. There have been many players who won millions and stake always sends cashouts instantly, no matter how much you win. They wouldn't risk their reputation by denying (legit) cashouts, it's what differentiates them from most fiat casinos. If you win a lot in a fiat casino they usually postpone the withdrawal asking for you to upload various documents while hoping for you to cancel the withdrawal and gamble the money away.