In that case it seems like it would be on the client to initiate the connection through Tor. I can't imagine a world where such a client would ever connect with such a server by default, unless that server exclusively stores content that would be fine on the clearnet anyway.

Tor has been around for ages but I haven't seen a lot of interest from internet users. I was a regular visitor of one website that experienced deplatforming/web hosting issues and had to move to Tor for a period of time. During that period, I saw the number of users drop drastically. Nobody wanted to use Tor.

Maybe it would be different if it was automatically implemented in Nostr; maybe it would catch on if it was more convenient. But personally I don't see the appeal of pushing to integrate censorship resistant media with Nostr. If someone wants to browse loli content, people have already found a few clearnet web hosts who will tolerate it. And if they are looking for actual CSAM/child pornography, I'm sure there are still plenty of Tor users and .onion sites sites that the FBI will never be able to touch.

I don't want Nostr to drive away their users and piss off the FBI all so that they can provide a service that nobody wants or needs. I say leave Tor media servers for when we actually need them.