I'm a trans woman.

Hey

i guess yes

Difficult question. I do think it could make things extra difficult but it all depends on the person you meet.
Lots of men are quite homo-phobic so the idea that you used to be their own gender could be an issue to them. Or the thought that your sexual activity was the same as theirs.
And maybe you can also come across guys that are simply curious to find out what it's like with a trans woman, nothing more.

And the biggest question... have you had gender-affirming surgery or not. If not... well, that changes the ballgame entirely.

You're probably better off asking other trans women elsewhere. A forum or community for trans people can likely give you clearer answers.

No

Nope ...not that adventurous !!!

IDK, is she rich?