That was our initial idea, but we realized most of the time you don't really know the person you are DMing with. Trusting them (and their relays) with the new npub (and the possibility of linking all your keys together) seems like a non starter.

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Very complicated but it's the only option for large (100+ppl) encrypted private groups. In theory, it requires two centralized services, which we don't have in Nostr. But I think @JeffG found a way around these restrictions. It would be great if it worked. I am still unsure what relays, the public and users can track from one another over time. But it will likely require a Tor-like IP hiding system to make sure relays can identify keys when the app is doing REQs with multiple filters.