I started to transition at the age of 44. Wife, no kids (fortunately), and a semi-public career.
I held most of the fears that you do about passing, still have my doubts, but after 10 months of hrt, passing is much less of a concern.
Hormones have been the greatest antidepressant. Seeing my body slowly shift along with my emotions has been the greatest confirmation that I’m doing the right thing for myself. I actually feel like I want to live now. I want to keep going.
As far you should go. Who knows? That’s entirely up to every individual. Some people find peace in the mere realisation that they are trans and make no changes at all. Others need to socially and medically transition as quickly and completely as possible before they’re happy.
There are as many ways to transition as there are trans people. Try exploring a little bit with your presentation and see how that makes you feel. Just feel it out step by step and see what feels right for you. At this stage I might suggest not even thinking about it as transitioning to female but more about figuring out who you are as an individual.
Personally, I got on estrogen as quickly as possible. Months before I came out to friends and family (my wife knew from the start). 10 months later and I’m pretty much still boymoding but in women’s jeans and T-shirts.
My look is becoming rather androgynous though. I keep getting “the squint” as people try to get a read on me. 😆
Best thing to do is find a therapist who specialises in gender issues. Mine was invaluable in the early months.