The @types/jquery package is maintained quite well so TS users can consume a typed jQuery anyway.
So, no plans to switch to TypeScript (or to ES6+ with the exception for imports) for now.
In short, I strongly doubt that the need for type assertions would meaningfully impact jQuery file size.
I haven't done any real testing on the jQuery code base but that's my experience working on some TypeScript projects.
A good point considering the scope of jQuery and its user base. I don't know much about generating larger file sizes but the community contribution aspect isn't something I considered.
So I made a simple TODO in like 30min. Naturally part of this is my familiarity with jQuery, the other is, for a small application jQuery is really great. I had a nice UI in no time.