I believe Keemstar is being honest about giving people those amounts of money even if the ideas don't end up producing any kind of profit, because he seems to be having some sort of mid-life crisis. He is bored, already has successful businesses that seem to run themselves, he has way too much money, and seems to want to recapture a feeling of challenge or secure a legacy outside of Drama Alert. I couldn't tell you the full details but as someone who has noticed Keemstar showing up everywhere trying to make weird deals and support smaller, more "controversial" streamers (like he did in the Bouldergate days) I can tell you something is going on there.
I keep feeling tempted to watch the Kino Casino on replay at faster speed + skipping, but you guys are making it sound increasingly not worth it. They really need to get one of their slaves to create a highlights/clips channel and post the best stuff to it, I'd probably watch that even if I never go near the main streams ever again.