I tend to think of the need to transition as being - largely - a matter of carrot or stick, and which is driving the person. Some would say the carrot is what they head towards, for me it was the stick behind me (pain). My life was not terrible, and if I had your concerns and considerations I might be in your position, but it was mostly pain and it was mostly empty. Having a fairly comfortable family life and dependents etc. is going to make it a more equal matter of carrot/stick unless you are in severe emotional pain. It's definitely a better position to be in; but there's more to lose.
When you only have stick, it's an easy decision.
If I had a wife and kids I won't pretend it'd be easier, even if I am fairly self-centered. I suppose it was clear to me (and to my partner) that it had to be done, because of the attitude we have - we don't have kids to worry for, we don't care too much what other people think and there's an unspoken rule that if one of us truly doesn't want to do something, we just say it and get it over with. If one of us didn't want to go do something with the other, the other would rather not do it that than go through a pretense of doing it. When I explained the problem, the response was to the effect "well I guess you'll have to do it then, or do something about it. Now I know you'd be faking life if you didn't."
...That didn't mean all was hunky dory with the situation, but it did at least mean we desired honesty, even if it was painful. In some ways I decided to go ahead with transition because I knew it wasn't going to severely affect many people at all, so I guess that consideration was a part of it even if I tend to downplay the aspect to myself. Almost nobody was going to be hurt by it, and the only person who was had already decided we weren't getting along great beforehand. (Ironically we get along much better now in terms of personality. Thanks, HRT). But the "clarifier" really was two things - 35 years of knowing that nothing I'd done or tried had ever got rid of my gender issues, and that I didn't want to regret doing nothing like I had done with other things in life that I'm still kicking myself for. I hadn't been able to go ahead and get a normal life really, that's pretty visible to most around me, so it did seem to indicate I have a real problem that I've never solved. Didn't seem like a vagary or just something I wanted to do. It seemed there was a tangible thing holding me back that if I acted might fix that.
I've mentioned this elsewhere on the forum but transition and HRT didn't simplify anything. It has helped immeasurably, but also complicated even a fairly simple life. My living situation and relationship, my family's relations to me, and it allowed me to see the internal feminine aspects of myself crystal clear even though they are largely hidden to the outside world. They will not be going anywhere, it seems. I'll have to make some kind of peace with them; I guess I already have done, but they absolutely complicate anything in terms of how I see sexual dynamics. Now I know that while transition can be a form of moving forward, and HRT does take the edge off, the true reality of my situation is that I've got hybrid elements in the brain. They'll never go away. How I go forward with that we'll have to see, guess I'll just have to roll with it. Simplest way to describe it: all aspects seem to be largely male save for a few in the sexual department. I can go through almost all everyday life without the "female" aspects arising there until I get to that. So I would advise, I guess... that if you have a dichotomy there that's currently still in the process of being weighed up, you're going through the same thing as I am. Realizing that being trans can be a hybrid state and figuring out how much of what state fits your everyday life best; HRT did make those states a lot more evident to me.
