> I was there for four households
Wait, how many houses does sky own?
Where does he get his money? Does he just leech/blackmail/threaten/extort others?
I've known Sky for an amount of time. Haven't talked to him in a good two years. Take things with a grain of salt as I don't have logs. He's made quite a bit of money, mostly from youtube/twitch ad revenue, twitch donations, sponsors, and being paid to go to events.
Events who know better don't want to deal with him nowadays. He either defaults on his contractual obligations (In one given case, he was drunk around event premises and didn't show up for panels he was supposed to do), or embarrasses the event for even inviting him.
The Amazon event was already brought up. I'm sure some people here might remember the Genesis 3 event where he made inappropriate comments about contestants, one of the more notable ones being the infamous "Oooh they hugged" commentary from Sky for a good 20 seconds. When that was brought up and communities reacted to his behavior, he swatted it away claiming that it's homophobia, his usual defense from criticism.
Having talked to him about his housing situation, I can tell you this is pretty much what he was doing.
Edit:
I'm gonna drop some more info. I wasn't terribly close to the guy and I don't think I have the Skype logs anymore so you'll just have to take this with a grain of salt. Since I'm rather detached from the Smash & FGC scenes, I think he felt some semblance of anonymity to me which allowed him to share things he might've otherwise kept to himself.
Then again, he also loves to talk so who knows? Maybe someone else can corroborate what I'm about to share.
Sky's financial situation is precarious. He refused to open up a Patreon and rely on fan donations as he felt he was " double-dipping " by playing ads and requesting donations. He's said as much on his YT channel but I'm not sure if that video is still public.
His main source of income from YT didn't come from adsense. It was sponsors. At least it was in 2018-2019. He did eventually extend to selling merch at this time but I'm not privy on to how much he made off of sales as it varies greatly from vendor to vendor. I do remember him landing a pretty substantial contract in early 2018 that would've allowed him to pay off part of his debt. Whether he actually did so or not is another question.
When I say he was not in a good spot financially though, I can not stress that enough. By the end of 2017, to the best of my knowledge, he had accrued $800K+ in debt. This is most likely from the 1st house he was living in and because of that, he kept having to find new places to live that would overlook his substantial amount of debt. I didn't know too much about his roommate situation so I can't really tell you anything there, sadly. I personally just assumed that they were all close friends / had similar interests (ie they weren't just random bums off of Craigslist). What others have posted though kinda fits in with the general vibe I got regarding his situation.
I can corroborate that he has a lot of debt. He loves to talk and he talks too much. He's very brash with his spending and doesn't seem to understand what a budget is. In 2015, he straight up paid a bunch of hotel rooms at an event on a whim. He wants everyone to see him as this helpful community figure. I think that's why he's been able to stay afloat for so long.
In spite of his supposed wealth/debt, he's a serial tax evader. At some point he owed the IRS 200k dollars or so he says, and went to cry on his Twitter as if that's the IRS' fault. His fans not knowing any better kept giving him money. Supposedly it is because he didn't pay the IRS taxes on his Twitch donations. Really makes you think about how much money this guy made.
He mentions his hardware as well, it was always of utmost importance to him to have the "best hardware" to make videos with, even though he didn't know how to use half his equipment, often relied on his "slaves" to do the work for little to no compensation, and didn't post any content for months.
If you've ever met the guy in real life, to say that he's a character is an understatement. One of the Google Docs mentioned that he gave people in his houses nicknames. He doesn't just do this with housemates, he does that with everyone, and many of these nicknames are not endearing.
Talking to him or even reading his social media, you'd almost be fooled to think that he believes himself to be the protagonist of an anime and wants people in his circle to know about it. He wanted to "spirit bomb" one of the people who posted google docs about him before going on his shitshow of a stream.