I don't have many complaints about the language itself, but I've found the packaging ecosystem to be the most complicated and frankly dysfunctional that I've used in the last decade.
Package management isn't a solved problem; Python employs standard patterns for it; Significantly better than chained Makefiles from my C-development days.
I always liked python, but I didn't use it at all really for a very long time until recently, and I've just honestly been surprised by the poor state its packaging seems to be in.
TS is just JS but with extra things that can go wrong (Babel etc) and not being able to use simple `require` syntax anymore and some not-very-automatic type checking that you don't need; I don't use it. It's like taking a steak fresh off the grill and smothering it with mayonnaise.