I agree that the general prudishness of dating and dating apps (especially for straight dating) makes this all more difficult than it needs to be. But as far as trans people are concerned, all I really see here is a lot of unnecessary worrying about improbable hypotheticals that aren't even that bad if they actually happen.
Very few trans people are likely to do a 'surprise reveal' because they know all too well that this can have disastrously violent consequences in a heavily transphobic society.
You claim that nobody is hiding information about their genitals. But while we can debate the semantics of "hiding", there are certainly lots of people who are not being open about that information. And I am arguing that the world would be a better place if everyone was just open about their genitals (and indeed their hormones).
It shouldn't need to be a big deal. There's nothing shameful about having genitals that don't match your gender identity (and that would not put me off dating someone).
Are large numbers of cis people really finding that trans people are contributing substantially to their difficulty in finding a suitable partner? I see no evidence of it. This concern is almost always raised in rhetorically heated threads about trans identity, in the service of a particular argument – but almost never in threads about dating.
It's not universal, but I've had conversations with quite a few trans people who considered it transphobic to care about genitals in dating.
That's just an anecdote, but as a more public example: consider that dating apps/websites let you select gender identity but don't have space for identifying physical sex characteristics, even though that is a primary selection criteria for many people. I consider this pretty ridiculous when a lot of these sites have a box for height/weight and even star sign.
> If you need to know about someone's genitals, you can just ask them before you meet them.
I think part of the problem is that you can't. There are lots of trans people that would be offended by such a question (and if they aren't, then why not just communicate it publicly in the first place!)
> the underlying reason behind all this is pregnancy and families, then there are questions you have to ask anyway. Not every cis man or woman is fertile or wishes to have children.
It's needn't be about pregnancy and families. It may simply be about attraction. For example, I'm attracted exclusively to biologically female people. I know from my past life experiences that this rule holds consistently, so if I'm looking for a sexual partner, then I don't want to waste my time making an emotional connection with someone who I then later find out isn't sexually compatible with me.