>Your question about "forever newbie" is really interesting to me, and I'd love input from people with more experience in software development (15+ years).

I'm 20+ years in and HATE changing jobs. The initial period where I'm Jon Snow (I know nothing) is always annoying and makes me feel like I'm not contributing at a level that supports my role and compensation. I find that it takes 3 months to start to understand conversations, 6 months to contribute to them, and 9-12 months to really be a consistent and effective leader of things.