Obviously the point of transition is to be yourself. The only way you know if it will be right for you is to actually do it and see if life is happier to live. I know that's captain obvious but the deeper meaning is coming.
At the end of the day, transition is better for you if you've *never* been yourself, and transitioning allows you to be yourself, making you less awkward and improving your social life. However, maybe things were awkward before, as you were yourself pre transition and that created a projection that did not match who you are. Transitioning may be what makes everything project correctly, and thereby making things less awkward.
IDK if that makes any sense but it does in my head

See, I'm transsexual (duh). I was awkward pre-transition, because I was trying too hard to be somebody I'm not. Now that I've transitioned, I don't have to try so hard to cover up who I am, or try too hard to be who I'm not. People have seen that, and I've personally won over so ... so... soooo many people that I never thought I would. My brother completely opposed it before, now he says "nobody in the family should have a problem with it... you're the same person just ... you look and talk different. You're still easy to be around, and you're less awkward because you're not trying to be anybody else anymore". This came from one of those good ol southern UFC loving heavy metal kind of guys. People come around if you are who you are... and if they don't, then they fall out of your life and you don't care, because your new life is
better.
At the end of the day you have to own whoever you are. People can see fake, they can see if you're trying too hard to be something you're not, they can sense if you're hiding something... they can see if something is just off about you (not physically, but socially). If you are transsexual, own it - be the girl you are inside and TRUST ME... even if you do get opposition, people will like you. If you're a cross dresser (NOT referring to anybody specifically), put on that dress and do what you do. If you're andro, sit in the middle and confuse the hell out of people. If you're bi-gender, switch back and forth based on feel.
IT DOESN'T MATTER! PEOPLE SEE WHO YOU ARE AND THERE ARE MANY THAT WILL RESPECT IT! EVERYONE ELSE CAN FALL OFF THE FACE OF THE PLANET! Your life will be much easier without them, and trust me, when you are you, people see that before everything else and will generally respect it.