So sure it is likely that in many cases browsers will still mostly see JS with stripped annotations, but the reason to do it is the same as the debate over whether or not to strip comments and/or support sourcemaps. There's clear wins at the very least in debugging situations to allow unstripped type annotations all the way through to the dev tools. There are even cases where that may make sense even in a production environment, including things like metaprogramming if those annotations are reflectable.
This nice thing would be to have the option, whether or not most projects might still prefer to strip them out to optimize bundle sizes. As with almost all things, it's an interesting spectrum of tradeoffs.
Are you really sure?
To me that attitude sounds awfully close to cargo-culting.
Microsoft has invested quite heavily into some very large TS codebases: VS Code/Monaco, VSTS, the Azure portal, large components of Office, large components of Bing, and so forth. Given the scale of some of those projects (in terms of users at the very least, even before you get into metrics like lines of code or dollars generated), that is a lot of benefit to having a strong tool like Typescript to do that work in. Many of the same developers working in Typescript use C++ and/or C# daily, so they already understood the usefulness of things like static type checking. Releasing it to the public when they did seemed a very cogent realization that that "enterprise JS application problem" was far bigger than just Microsoft and they were in a good place to help with that, given it's long been a goal of the company to help developers.
As for a Typescript proposal for TC39, I'm willing to bet everyone is still worried about accidentally creating a second "ES4" debacle, including Microsoft. I'd love to see, and would much more expect at this point, a pragmatic compromise like Python's PEP 526 [0] / PEP 3107 [1] project, encouraging JS engines to syntactically accept things like Typescript's type annotations, but remaining agnostic to what the annotations represent semantically (giving other JS users the option of doing things with the annotations other than types, too, if they wished).
[0] https://www.python.org/dev/peps/pep-0526/ [1] https://www.python.org/dev/peps/pep-3107/