Yeah, why session over briar? You've brought up publicly the problems with session and big rooms, briar is p2p with forward secrecy.

Trocador... I like trocador. But there's nothing stopping them from logging everything, they could be a honeypot. Their monero bridge is great, unless theyre using it to make themselves valuable to people who want to know what you're doing.

I've never liked libredirect, I found it cumbersome. I use Redirector, a web extension for ff and chromium that automatically changes URLs based on predefined patterns written in regex. On desktop I use my own tool with qutebrowser that does something similar to be found here https://codeberg.org/mister_monster/qutebrowser-url-mutator