Earlier quoted context omitted.
I'm definitely choosing path 1, which is to become a senior dev. I prefer technical-focused jobs. Learn from mentor programmers, get into teams and learn formal development practices, and then help out programmers less experienced than myself. I've never held a senior title, never led a group, nor even been involved with the process of hiring other programmers. I currently live in Chicago which is pretty good for COL…
In that case, I'd recommend specializing in one particular language/framework/domain. Whether it's NodeJS, Python, C#, Swift -- pick one and run with it. "General programmer" is fine for management but not great for senior developer. It seems little odd that at 35 you're still in the $25/hr range. Either you got a late start or maybe there's some soft skills you need to improve (running a meaningful meeting, developi…
Don't underestimate the negative effects of having no job lined up when you're let go from your current one. You can't realistically negotiate for an ideal salary when you're currently making zero. Taking a less-than-optimal job offer is still better than being homeless, though.
For reference, my first web development job paid $12/hr (part-time) in 2007, in the Chicago area. I found this job by cold-emailing job listings on Craigslist.