Welcome to the Café Stefan.
stefan wrote:I guess I can see 2 big hurdles in the future.
Wearing skirts when meting friends / family
Wearing skirts for work
How you deal with these will be a decision you have to make for yourself but I will share my experiences and maybe they will help you in a small way.
Friends and family were just like the rest of the world in that the fear was far more of a problem than the reality. Let's face it, what we wear does not change us so if we have friends when in jeans they will still be friends when skirted. However they will almost certainly want to tease you about your attire for a while

. I simply refused to rise to the bait, made a point of referring to my skirt (even when kilted) and pretty soon they got over it and, if anything, became too inclined to jump in and defend me if somebody else wanted to join in the mickey taking (at 1.95m (6'3") and 104Kg (230Lbs) I generally don't feel the need for others to stand up for me). Family were just the same, apart from my wife who was a little harder to convert. This is because she felt that how I dressed might reflect on her to some degree. I simply wore kilts or skirts at home and restricted myself to kilts when out with her as she seemed to find that less problematic. Over time she got so used to the skirts at home that she did not notice me wearing them when we went out together. Problem solved.
Work was a different situation. My colleagues were just like everyone else and so no problem, but my boss was concerned about how the company would be perceived by customers so he was not happy for me to wear a kilt. I compromised and stuck to the company dress code while he was paying me but dressed to suit myself (or the task in hand) when I was in the office in my own time and while travelling to locations such as our overseas offices. This was accepted, although I had a few curious looks from guys in the Spanish office and eventually one asked why I wore a skirt when arriving or leaving ("because it is more comfortable"). No further comment was ever made since it was obvious I was comfortable and did not see it as a big deal.
In summary, your two big hurdles may not be as insurmountable as you think, just like wearing skirts in public wasn't.
Hope that helps.
Have fun,
Ian.