Great topic. Yes, I would have been happier. I spent my tomboy childhood, wanting to be a boy, complete with physical attributes. None of my friends were into 'girly' things. When I reached puberty, I wished I could have an operation to remove all the bits and pieces to do with bearing a child - I knew I'd never need them. When I was a student and fell for all the gay guys, well, yes, life would have been much easier if I'd been a guy myself, instead of being rejected all the time. My years in the military would have been no different on a career level, but the bloke-me would probably have done a lot less sleeping around than what the real-me did, in a weird attempt to hate and abuse my female body. And now, I would definitely be a lot happier in a bloke's body. It's only since I moved here that I've started to realise that I'm not who I thought I was. It would be so much easier if I could start all over again in this town, but in a different body. The folks here just aren't ready for people who don't fit 'the norm'. They're just about coming to terms with regular gays!
And as for the future? I really can't imagine not being lonely, either in the near- or distant future. How the heck does someone like me find a companion?