It's pretty simple to get TS building via webpack for react, and tsc itself has a watch mode. The only PITA there is if you save any breaking changes, the build will obviously fail until you've completed and saved any the working changes, but at least you can't forget.
I seem to forget to save sometimes also (granted, that would mess me up with javascript also), I'm just so used to straight C# in Visual studio!
Typescript also isn't a very fast compiler, it doesn't seem to be incremental or retained at all, so when you build your project, it take a few seconds when your project has grown beyond a certain size. Sometimes I build and then hit run too early (before the build is actually finished).
I'm using webpack on a ~60 TS files project now. It takes a few seconds to bootstrap, but then, in watch mode, it only compiles the files that are changed and it's really fast.
It's pretty simple to get TS building via webpack for react, and tsc itself has a watch mode. The only PITA there is if you save any breaking changes, the build will obviously fail until you've completed and saved any the working changes, but at least you can't forget.