I'm in my 30's and started towards transition 2 years ago (when I first started seeing a psychologist about it). It's hard for me to hear of these younger guys underage and/or still at home dealing with that. It's makes me grateful I've lived out of the house for quite awhile and am financially stable (hope to stay that way). That's a plus for most older guys.
I did have concerns about my career but I seem to be somewhat safe where I work now. I do look forward to working somewhere else where I can start out being male. People's "slips" of pronouns at work are getting enraging. In fact, it seems worse lately. It just makes them look stupid to other people. You'd think they'd learn. I had concerns about contacting my past employers so they could update my name and gender. I need them for my resume and references for job searching. Surprisingly they were all supportive and- to my knowledge- updated my files. So, I've lucked out there.
My family who knows so far have been very supportive. I think at our age people realize we know who we are and know what we're doing. People seem to have a stereotype that younger people don't know themselves and everything's a phase. Several pre-transition friends have been good about it as well as new friends who know.
My biggest problems come from my ex. I lost all our mutual friends and his family. They were his friends first so of course they sided with him (as I guess they should). I have no idea if they know I'm trans or not (friends or his family). Every time I see or talk to him (which thankfully isn't alot) he always acts angry and tries to make me feel like crap. At first I was hoping we'd be friends, but he just wants me dead. After everything now I don't want to be his friend.
I've lost alot from the divorce, but that seems to be normal for the guy

. Seriously, he was way more the "woman" in our relationship than me. I look forward to the day when I can break myself from the house and move on. I definitely want to move to a different city/state and start fresh... mostly because of him. I'll miss my friends but my peace of mind outweighs that.
So, there are pros and cons to transitioning later in life. I
do regret getting married since that definately postponed my transition. But, I made those decisions and just have to accept that. I can't imagine having children in the picture, too. I admire the strength of those who have kids involved. I'm sure that brings up different problems and road blocks, but you all seem to get through them.
Oh, another con for me was it seemed T changes took longer for me than for the younger guys, but I was told that might happen. It took longer to pass all the time too.