These are good questions. It’s good that you have a threat model. I’ve been there, and I came to the conclusion that trying to hide and never make a single mistake isn’t worth it if the state is your threat model. I tend not to underestimate the state. They can be very incompetent, but I think if the state really wants to find you, they will, unless you’re diligent 24/7. And I already have sleep problems.

So either what I’m doing isn’t worth their interest anyway, or I’d have to live a life I don’t want to live.

when has attaching your reputation helped

In my case, it helped in ways I wouldn’t have imagined. Two examples:

1. I gave a talk at bitcoin++ in Berlin. A few months later, in Brazil, people recognized me and offered me the opportunity to be a mentor for new bitcoin contributors. I was very surprised that they even knew my name: “You’re considering me? Thank you, but why?” “Because we saw you talk in Berlin. You know enough about bitcoin to talk about it on a stage.”
2. My Signal link is on my website. A VC reached out because of a prediction-market prototype I built many years ago and put on GitHub. I’m not sure they would have bothered to reach out if I had been trying to hide my identity.

YMMV