I had a stint of about 2 years of job hopping every 3-6 months at the beginning of my career. Worked great for me every time.
The trick is to get the new job while you still are employed, not quitting and then looking for something new. Employed = attractive to other employers, but still a bit of a red flag. Unemployed = just a big red flag.
Once you cross the 5-7 years of experience mark companies will start to ask the question more pointedly as 1.5 years roughly corresponds with a performance review cycle. We all know engineers who have failed upwards or outwards for years but are competent enough to pass an interview and personable enough not to be fired. Senior level positions also tend to involve multi-year commitments that the company needs to know you're onboard for.
If I were you I'd try and get one solid year of a job on my resume, to start with. You said you're worried about becoming homeless anyway- why would you quit a $15/hour job if you don't have anything else lined up? Unless it's just a really toxic/destructive situation, that seems like a mistake. Paying the bills for the time being and building up some solid work experience seem like aligned goals right now. The healthcare thing is unfortunate (it's unfortunate that anybody in our society has to be in that position), but I don't think quitting without another offer is going to help.
Best of luck.