ii) Lots of libraries are extremely well documented and typed. This is the same in any language not just for types but also for docs, capability, perf etc. This argument applies to all software everywhere so it doesn't make sense to single out TS
iii) Error messages can sometimes be hard to follow. But you get better at parsing them very quickly when they get gnarly.
iv) Transpilation is nearly always a required step anyway. Adding TS support is minimal. There are plenty of tools that do TS to JS on an order of magnitude of MS.
All decisions are tradeoffs.
What benefits does it bring (ignoring the biggest one of them all)?
TS makes it easier to maintain software across large teams by providing a mechanism to express relationships in a codebase.
They are self documenting and replace a lot of JSDoc needs (letting you focus docs on more useful info like intent, design choices, example usage, etc).
Types can also replace the majority of unit tests validating code is correct saving time on running fewer unit tests and letting devs focus on integration tests.
Lastly, I've never seen or experienced something breaking from upgrading the Typescript version in a project. Even when a TS upgrade has 'breaking changes' they never actually break anything in practice that I've seen.