TypeScript's strong part is the IDE support. It worked great with Eclipse years ago (using the same language server), it worked with Atom years ago. It has Sublime plugin that also uses the language server (not tried this myself). This is because the whole language is build with IDE tooling in mind. It's also approachable, as more language servers are being built the same way, like the PHP language server that is now gathering steam and will be used in several IDE's also besides VS Code.

Webpack and fancy loaders could be issue if you want type checking on really fancy syntax plugins. (Not sure what they are, since JSX is part of TS) These days you need one Webpack loader anyway for new ES features. It's really great that you can just remove Babel and use ts-loader in place as many of the ES features are already in TS.