I started transition at 31, ended at 32 (and GRS at 34). I have been fortunate, in that I'm very happy with the overall results from HRT, and I was taken for female "accidentally" - dressed as and presenting as male - by around six months into it. It was 3-4 months before I could pass when dressed up and looking female, I think? Anyway, the amazing thing to me has been that HRT makes all these tiny, subtle changes, so small that you can barely identify them, but it all adds up to this largely subconscious "this is a woman" signal to everyone around you. I wouldn't say I'm pretty enough, but that's the societal pressures on women, as you've said; I think most women wish they were prettier.
I was also lucky enough that my wife stayed with me and my job was very accepting, so I can only wish you luck there.