If I were you (which I'm not!) I'd take one thing at a time, rather than trying to plan your entire life all at once. Start with your marriage. You say you're recently married? Most marriages, as many as 90%, fail after transition. How many fail WITHOUT transition???
Before rushing to have children before it may be too late, by all means, utilize a sperm bank before beginning HRT. If your marriage fails, you won't have a child to deal with, and if your marriage flourishes, nothing is lost.
Whether or not you transition should be thought of separately. People usually transition because they HAVE to transition, not because it seems like a convenient time. Transition is also a very expensive process, so is being a parent! It's going to be very difficult for your wife to deal with your changes at the same time as rasing a child. Is it fair to burden her with so much? Your wife will be going through changes too, as she becomes a mother.
I know you've said your interest isn't really in cautionary tales, but I just can't think of anything other than caution. Can it all be done? Yes, of course, but if nothing else, wouldn't you be better off waiting a little, and doing one thing at a time? Stabilize your home life, have a child, or two, and THEN, when everything is stable, think about transition. I'm not saying not to do anything, by all means, do what you must, but do everything in a less hectic manner which will be more likely to lead to comfort for you and your family with a minimum of stress. Your age allows you to pace things accordingly. I understand you have things you'd like to do, but you really don't need to do everything all at the same time. You can have a family while saving money towards your transition, you can also have your family while beginning laser or electrolysis, after having children, begin HRT, it's a slow process, or you can also begin training your voice; you DO have options that would have minimal impact on your home life.
How will transition affect your ability to find employment?
