One of the main reasons I think Phil is doing just fine financially is that we've very rarely seen Phil in panic mode. What are things we'd classify as Code Red situations for Phil? I'd argue "any circumstance that warrants a Reeemergency stream", mainly because they feature zero gameplay, only talking to his viewers. Now, I think a reasonable argument could be made that he's not playing games because he needs to give 100% of his focus to whatever story he's spinning, and I think that'd be a good argument, but it's also Phil putting more than the bare minimum of effort into something, which we know he doesn't do unless he feels he's forced into a corner. So even if these "let's talk" streams aren't necessarily filled to the brim with truth, we can safely assume that something is driving him to do them. Any other begging he does (Minecraft whinging, Blackout toilet time) is just bog-standard, "I want munny", Page One out of the Phil Burnell handbook.
Going by that metric, we haven't seen Phil in truly dire straits for a while now. He hasn't felt a real need to be ahnest with his viewers in a while, which leads me to believe that things are just hunky dory, and when he brings up being overdrawn for the fifth time in a month while he's aimlessly meandering around some video game it's just touching on the pressure points he things will open wallets. There's no truth to them at all. When Phil wants to sit down and talk plainly, that's when people should sit up and take notice.
Just look at the lies he tells: zero effort, no further elaboration given nor offered, and the same handful of stories over and over. What reason does he have to change anything up? He gets the sympathy quarters he wants no matter what. If he was on the brink, he'd only be able to go so far not to show it.
That said, "the brink" is different things to different people. Phil has a lot more to lose than some Twitch affiliate living alone in an apartment in Kansas who just streams for fun or to supplement income, and on top of that he's got an entire legion of people waiting to see him fail. Any desperation move he makes has to be couched in language and behavior that still makes the worst case scenario not sound like the end of the world. Think about all the times he's talked about losing the Wakhando. Has he ever once spoke about it in terms of being homeless? No. It's always "I might have to move into a smaller place". While that might be disastrous for him, it's only because his ego can't take the notion of the one-two khambo of losing his Real Adult House and having to go through the physical effort of finding a different place and moving. He knows he'll never be living on the street, and so DEFCON One is all things that pull back the curtain on what an incompetent, unfunny, milquetoast moron he is.
This post is getting away from me so let me tie it back to my original point: Phil will leap into action if and only if he has no other option, and he has to be so careful about it that a blind man can see it. "Nothing draws attention like evasive action". When Phil is really in the shit, we'll all know because he'll be up on that diseased loveseat turning cartwheels to talk out of both sides of his mouth. He needs that munny, dood, things are bad. Oh, are you gonna lose your home, Phil? Is Jasper going to starve? Are they going to turn off your power and water and cut down your internet?
W-well, n-no, I still got it all under control, huhuh. I just..really need that munny right now, you know what I mean? Anyway, here's how you can tip me...