If I'm having sex with someone, and I'm very allo so that's my assumption going into dating, genital configuration is important to me. I like cock on masc-presenting folks, so chances are cis men are exclusively where I'll be wanting to date. If I were a little more bi/pan/ace, my answer would likely be different.

As long as it's post op, sure. Only reasonable issue I can think of is no kids, but I don't want kids anyway so there is basically just no issues.

Yes.

That's such a weird order of operations. Like, your medical conditions are simultaneously such a big part of your life, and yet also so deeply personal that it feels like they should not be part of the initial conversation, which is supposed to be shallow and light, not immediately heavy duty.

I think perhaps there are other more important considerations than mere trans-ness, like "do they have the same overall life goals that I have" and "are they taking care of their mind and body and fitness". But transness may inform those aspects. If a significant focus of their life is on their own gender, I might struggle with that. If they're already at a point where they have dealt with it and moved on to other things, then it might work. If they have comorbid issues beyond transness, like depression and anxiety, that can be a deal breaker unless they are managing themselves and putting in the work.

Probably not because I'm attracted to biological females. And this is not an "issue" that I need to navigate so yeah it doesn't really matter.

I'm bi, and also trans, so no problem, lol