Anecdotally as someone who writes a lot of Typescript - which has a very expressive type system, most of the time when I need to help someone who's "fighting" with the type system the issue is that they've written a bug but the error message just isn't particularly clear. Which is loads better than them writing a bug and then only discovering it in production.

Mentally parsing the type errors is an art though - generally you want to ignore pretty much all but the bottom 1 or 2 lines - the rest is a bunch of very verbose information at a much higher level of abstraction than you care about.