This is a bit off-topic but I was reading some time ago about Dan/Dani Bunten (of MULE fame, among other things), who had gender reassignment surgery. More info here: http://ai.eecs.umich.edu/people/conway/TS/Warning.html#Dani but this is what I was reminded of:
"Despite following the rules and being as honest as I could with the medical folks at each stage, nobody stopped me and said "Are you honest to God absolutely sure this is the ONLY path for you?!" To the contrary, the voices were all cheerfully supportive of my decision."
No one really challenged Dan at the time - possibly for fear of being labelled as a bigot or hater or whatever - and Dani later regretted the decision.
Again, somewhat off-topic, but finding people to really challenge you (in a supporting way) is hard to do.