By contextual data I’m really just talking about things like being able to auto complete from it only the code base, but associated sql schemas as well. Or presenting code navigation as a sorted hierarchy of classes, functions, etc. Lazy human want computer do work.

What he wants is to connect his editor to an SQL database and have TAB completion in a string for keys and tables in that database. He wants to be able to traverse a codebase by classes rather than by file. Basically he wants Smalltalk.

I'm pretty sure Emacs could do that even with org-mode.