This has been a dream of mine and one of my friend’s as well. There’s a small handful of blockers that I’ve slowly been transitioning but the upcoming windows pain points you mentioned are definitely recent motivators for me. I’m glad you made it and I hope the rest of us can too! I look forward to reading more about your experience.
I’m a little of both, I joined for escaping the reddit blackout shutdown, but I stayed for the advantages of the fediverse. I grew up working with a lot of proprietary software, and I’ve had growing pains as I’ve grown bitter about proprietary software over time. I’ve been self hosting, working on migrating my machines to Linux, and trying to find workable alternatives to everything.
Edit: yes I’m quite techy, a DevSecOps/software engineer. I worked with Linux a long time through VMs and containers, but gaming and Adobe kept me from having a daily driver machine for more than a little while. I don’t think I’ll ever fully escape Windows because I’m a big .NET developer and work with a lot of legacy code, but I’m more than happy to leave that to a QEMU VM.