On your wishlist items:
1. There are a few third-party projects that bundle Lua code. One that comes to mind is https://lrocket.codeberg.page/ — I don't know if this functionality should be brought into Teal itself, it sounds to me like something better left to the surrounding tooling?
2. Unfortunately those annoyances are part of the heterogeinity of the Lua ecosystem, but Teal tries to paper over them using the compat53 library (which, granted, is not available everywhere if you want to do a pure-Lua deployment on existing Lua environments). The --gen-target and --gen-compat flags should still help some, hopefully!
3. Not sure what you mean there -- you mean adding chunks of untyped Lua _in the same file_? I think that if you have a json.lua and a json.d.tl file, then it should use the definition file only and leave the .lua file alone. At least that's the intended behavior!
4. That's up to GitHub :) Last time I checked their docs I think they want something like 100 or 200 projects using the language for considering adding native highlighting for it on the website. But you can add a .gitattributes file to the root of your repository like this https://github.com/teal-language/tl/blob/master/.gitattribut... and at least it will display .tl files with .lua highlighting.
Again, thank you so much for the feedback!