in one of the streams of his i caught, he was in his car shortly before going homeless, probably a bit drunk, and he was more angry/unhinged than he usually presents himself in his videos. he was straight up talking about how badly he wanted to deck his mom in the face, for example. he definitely has less of a filter when hes streaming as opposed to recording a video, which could bite him in the ass if he ends up saying regrettable things. it could have been the alcohol, though. and you are generally right that he doesnt exhibit too many lolcow red flags, particularly the fact hes relatively self-aware and doesnt have a huge sense of entitlement (well, some may argue that point but he definitely doesnt feel entitled to money)
we'll see how it goes, but the one thing for sure is that he'll make farrr more bank than he would settling for another warehouse job. he may not have a huge viewer base, but the 25k subs he has are loyal, so i imagine a decent chunk of them will sign up for a membership, and he'll likely get a few whales who dump huge amounts of money on him if he livestreams. its the right way to go if he handles it correctly.