I definitely prefer the TypeScript dev experience for larger/longer-term projects, all else being equal. You spend an hour or two configuring your build tooling

I definitely prefer the TypeScript dev experience for larger/longer-term projects, all else being equal. You spend an hour or two configuring your build tooling and then don't really have to mess with it much after that. But I also never bother setting up TypeScript for JS one-offs or scripts (where I would bother to add Python type annotations in those cases), so make of that what you will. Deno is currently trying to bridge that gap - putting TS directly in your interpreter - but right now it comes with some caveats around being a separate runtime with incompatible system APIs, unfortunately. We'll see if it takes off enough that that becomes less of an issue. Aside: > it's a problem made difficult by an accumulated legacy of unfortunate decisions and there just isn't enough investment to move it forward This is funny to me because JS has an even bigger accumulated legacy of unfortunate decisions, it's just gotten an obscene amount of investment to move it forward despite all odds ;)