1. We've been exploring migrating one Optic skill to a newer version. So far it seems promising for the cases you'd expect a code-mod to help with, but if you completely change the API and deprecate some stuff it can point out the changes but won't be able to help you -- no magic here.
2. I looked into language servers (lsp) but the implementation was a lot more involved and I found bugs in some of the IDEs that claim to have full lsp support. As the protocol matures and we add more functionality to Optic I expect to see lsp become our main avenue for IDE/Optic interactions.
3. We wanted to make it really natural to ask Optic a question. We thought '///' would be unique and easy to remember, but we're open to changing it. It's nice that '///' also evaluates as a comment too because before we used it sometimes characters in your search would cause the AST parse to fail. We're open to any ideas here -- a lot of users have said it's funky.