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?

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

Having been heavily participating in the onchain summer tasks on coin base wallet I'm becoming more  and more familiar with the ins and outs of how it's all coming together. I would and do now check that messaging inbox pretty regularly now, if that is any positive support/answer to your question