In my experience, most people can receive NIP-04 messages, while only some can receive NIP-44 messages. And the problem which you've correctly pointed out is that if you send a message the recipient can't receive, you never get any kind of notification so you just have assume they got it, or not. There should be some mechanism to alert when the recipient doesn't accept certain message types. Or some sort of fail over where it tries NIP-44 first, and if it fails, falls back to NIP-04.

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