I don't have a lot to add except that my experience with it has been very positive; your complaints are mostly valid, but for me those pain points disappear in the shadow of all the things I no longer have to spend time stressing about or debugging
If you’re learning JavaScript or any components of the language, you’re better off just starting with typescript (given the technical acumen up front).
It’s absolutely a no brainer, long term roi. If presented the opportunity to integrate or use now vs later.
The community is also very active, and it’s under Microsoft - and has been well maintained and quite active. Lots of libraries.
It depends. The tooling is still a barrier (even though it's gotten smaller); the cost is small for a real project, but for someone who's learning and knows nothing about the ecosystem, it could be a real obstacle to dive all the way in at once. The exception would be if you're starting with something like Deno that integrates TypeScript seamlessly. Outside of that, tools like esbuild have significantly lowered the bar vs a few years ago when you had no choice but to configure webpack + babel. But even esbuild isn't quite zero-configuration
If you're just starting off with JS or TS you shouldn't be messing with tooling at all. Just install one of the many create-react-app derivatives, run one command and start developing. All those boilerplate generators support TypeScript now, too, so you don't even need to do anything extra to start using TypeScript. Even TypeScript itself can be incrementally adopted since it's a superset of JS.
You will outgrow those app generators, but for a learning project? There is no need for you to even see a webpack file.
