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Also the same in login, I connect with TW, enter my password, I get to desktop, I quit TW it locks my pc again to password screen and can not stream my pc to Steamlink because it's locked.... Just drives me crazy
That said... Steam should be able to gracefully handle DirectX/VC++/etc first time install stuff through the admin level service it has for exactly that reason. You shouldn't get any UAC prompts from Steam for the first time setup of a game.
A headless setup isn't strictly impossible, you just need the computer to think there's a monitor attached. There's literally a pinned topic about this.
Deleted my post because you are correct, but for me it's impossible due to the GPOs in play on my home domain.