I think the thing you neglect when having setups like this is that you start to garner interest from law enforcement if they ever come across you. You're trying so hard to cover your tracks that you stand out very clearly in a crowd.

There's a middle ground between living deep in the woods without windows and walking around naked in public.

It seems you are talking about Social Cooling, https://news.ycombinator.com/item?id=24627363. The more people like me exist, the easier it will be for actual activists and journalists to do their work. Privacy and anonymity are crucial for democracy.