Good questions, Lucky.
When I was in my twenties, even though it was after Stonewall (just barely), I was happy being gay. But those responsible for deciding whether I'd be successful in climbing the corporate ladder in the Fortune-500 company I had just joined would not have been happy. No doubt I'd have been sidelined. Far from an opportunity to be a corporate trailblazer, I'd have thrown away a career I was anxious to build.
I came out to family and a few close friends. But I wanted to be successful in the workplace based on what I could do, rather than who I slept with. So my choice, forty years ago, was to keep my life compartmentalized.
I don't walk in Chace Crawford's shoes, or anyone else's. I don't know what his advisors are telling him about the career effect of coming out versus letting his preference remain a topic of conjecture. Only he knows that. So, personally, I'm content to let him make his own decision.
If he wants my advice, he knows where to find me.