Like Jack Benny I am perpetually 39.
Problems? Challenges? Oh I've had a few. With age comes wisdom. Plus perhaps a bit more patience. As an old geezer you have a lot of life and living under the belt. In many ways it can be a bit more of a challenge then for a younger person just starting out. At the same time, as a younger person I "Experimented" with transitioning twice. Both times utter fails thanks to a ton of baggage, shame, guilt, internalized, transphobia, and No Tools to help undo all that damage.
No in my dotage, the time came several years ago to take the Trans-Beast on for real. It was far from easy in the beginning. Even more baggage, shame, guilt, internalized, transphobia, and No Tools to help undo all that damage, plus a lot of life under the belt. Like a wife, a career, plenty of financial obligations, etc.. Not anywhere near as simple as just after finishing college. At the time any sort of transition was off the table. I just wanted to try to heal myself. Part of giving up years ago was at 6ft tall, big everything, and balding since 14 I stood no chance of "blending in" in a world filled with 5'6" tall women. All that stuff sure didn't change with age... OK the height of the average woman but that's a stretch.
As I worked hard to fix myself from the inside, what was on the outside mattered less and less in that the sheer joy of being out in the real world as the real me mattered far more. Seven years later I'm still present primarily as male, still have a wife/bff/reality-therapist who loves me far more now that I've grown so much as a person. Yes, there are other growth areas she is not too fond of. We both make compromises. Life is about balancing a multitude of conflicting needs, wants, and desires to obtain the best outcome. Wisdom obtained through age allows you realize there is no "Ideal" outcome