It's rare for there to be a breaking change in the JS emit.
The TypeScript team work hard to preserve compatibility. Breaking changes are explicitly managed and communicated ahead of time. There is a concept of a breakage-budget per-release. This means if you stay up to date, the cost of each upgrade should not be huge. Orta and Nathan on the TypeScript team talk about this in this podcast episode: https://dev.to/devteam/devnews-s1e4-typescript-4-0-gitee-chr...
So "keeping up" is not too hard.