As for teaching JavaScript’s pain points... that’s not really how I operate. I’d rather they know the general rules and come across edge-cases when they’re in a position to solve them, rather than overload them with information. Automatic semi-colon insertion is powerful enough to get you through several large-scale projects, so there’s essentially no point to discuss it prematurely as anything but a curiosity, “this could be a gotcha, so keep your code clean”.
Finally, comparing the error linters in VSC for Python versus javascript, especially if you //@ts-check... I think JavaScript actually does a better job.