I want to become one of you, and I might have the ideal setup to try it but I have questions

I tried making a throw away account for this but it didn't have enough karma.

I've been working the same software engineering job for 8 years now. It's a very chill company even though it is very small. Honestly, I've stagnated a good amount just based on the small workload expected of me over the years, but I've certainly accomplished enough to even be promoted to a more mid/senior level position.

The pay and benefits aren't great, but again I often have a very very small workload. I only have two meetings a week right now, once on Tuesday mornings and once on Friday mornings. We only use discord for communication, and github for project management (open source company), and our company emails for user support. I don't know if my coworkers even have a linkedin account.

I have medical insurance that's pretty basic and barely includes vision, I have to pay for my own dental insurance separately. No 401k or retirement benefits through work, separately opened my own Roth IRA account this year and have no other investments.

Is there anything I need to be careful about? Like having two health insurance plans? Or taxes? I'm a single W2 employee with no assets or real investments.

I was diagnosed with an autoimmune condition and some other chronic health problems this year, so I'm wanting to buckle down and try to secure some kind of safety net for the future while I'm able to if it's possible as I have no real family or financial support from anyone else.