To be fair, part of the issue is tied in with the SIN system.
If you are SINless you are not supposed to be able to go out and rent a regular apartment or all the other normal day to day stuff.
For some the Squatter lifestyle is how they see their characters being, since even a Low lifestyle requires some kind of SIN in play.
So they are renting a coffin at the motel for the night or hanging out in some abandoned corner in the Barrens they carve out for themselves.
It's less about crowing about how much money they are saving and more about being stuck in the bottom rungs that money alone can't buy your way out of.
Should Squatter be easy living? Hell no, you have to scrap for what's yours and travel pretty lightly, but it still miles about living on the streets entirely.
I had a period in my life where I fell between those cracks and lived like that for a time. It's somewhere you don't want to stay, but for some it is not so easy to claw their way back.
One buddy basically burned his life thanks to a short temper and loads of outstanding warrants resulting from same so he will never be coming back out of that lifestyle because jail time would be the only thing he could look forward to.
Thankfully the Keys are not the worst place to be homeless, least the weather is survivable and there are plenty of folk who pay cash under the table for odd jobs.
But it is still a shitty way to live, so yeah a GM should play up those aspects to reflect the hazards of that style of living, but don't make it totally unsurvivable either.
Of course the answer for a Player is to just go get a SIN, which for most runners is usually a fake, but then you need a minimum of three really- one for your day life and a separate one you use when running and the third for when things go tits up and you make a run for the hills. And that is not taking into account the usual turnover in burning a SIN or two along the way.
It does sometimes seem like the heavy prevalence of fake SINs (I mean you are not just getting one, but 2 or 3 at least) just sort of undermines the dystopian feel though.
So you do get more runners who can go grab a better lifestyle, but some will still want that grittier feel to their character living on the edge rather than basically playing Zorro- bandit by night, respectable person by day.