I've been using semicolon-free Typescript a lot lately (and really liking it that way) and its transpiler is ASI (automatic semicolon insertion) aware so it ends up adding the semicolons back into its JS output, which you can use as a safety net if you are worried that you don't quite have a handle on ASI.

That said, JS ASI is not much different than Python/Coffeescript newline rules and if you are comfortable programming semicolon free in those languages there shouldn't be a reason that you should feel uncomfortable going semicolon free in Typescript and/or JS. The nasty issues are in fact mostly the same as Python/Coffescript.