One of the most frustrating things is seeing someone's ENS and wanting to reach out to them but having no means of actually doing so.

Pasting the ENS into FC/Twitter/Telegram sometimes works but otherwise its just a dead end connection.

What's the latest on onchain messaging and how to "DM" someone to their wallet?

xmtp

Onchain is the new online - FID 206 -  cooprecords.xyz

/xmtp is probably closest, but lacks widespread adoption

sending an eth transaction containing a message might be the most effective way to reach someone assuming they have transaction notifications on for that account