It would not surprise me at all if Caitlyn winds up not as happy as she imagined. Don't get me wrong, I'm not wishing her ill. I don't see much in the way of signs of amends having truly been made for the suffering others went through as Bruce repeatedly made decisions prioritizing himself. While he was no doubt unhappy all these years he time and time again made life altering decisions to try to make himself happy that involved other people -- and had no compunction about dropping them when they became inconvenient to his happiness down the road. IMO it's very telling when Bruce and Caitlyn have stated that this has been put off too long in the interest of other people and now it's her turn to be happy. You've ditched 3 wives and 4 kids along the way. You're trying to hide behind being father of the year while waiting for the two youngest to be out of the nest? Tell the whole truth, at least to the people you wronged.
All of Bruce's issues and unhappiness cannot be laid at the doorstep of gender issues IMO. I have the feeling Caitlyn thought she just needed the opportunity to tell her story, glam up, make some more $$ to insure her future and, whammo, the future is rosy. If Caitlyn isn't more skilled at real empathy and caring for others she won't have friends and be lonely just as Bruce was.