Aye this was a good discussion. I'm not sure if I'll go with NIP-29 as it is or not, or go with something custom, or perhaps a meshmash of things (and present the user with "here are your options with their pros/cons"), to eventually reach discord's level of service, all the while considering the nature of nostr, is definitely a challenge, with different trade-offs depending on what's chosen. It's definitely worth exploring different solutions i'd say, where a bunch would make products based on NIP-29 and advance it, others might build on top of a modified NIP-29, others might try something completely different, and I guess we'll see how it fares as we play with all of them and see what works best in practice. I'll probably spend a few days thinking what I'll do on my end, digesting this discussion before moving forward.