So I think I'm feeling near ready to meet some other trans people in person and join my local support group. The problem is I have never knowingly met a trans man in my life and the idea of meeting other trans men in person who may be at various stages in their transition still scares me. I don't know why though.
This was a fear that I had as well. I felt like they would make me feel inadequate, since I was not very far in my transition. I found that in my case, the opposite was true. The trans* people that I have met have helped me find therapists, price hormones and become more comfortable with my trans* identity. It's always scary to meed new people, but it's nice to have a support group that you can talk to in person. So, I would suggest that you try it out and see how it goes If you don't like it, you don't have to go back.
I felt the same. The only way to get over it is to jump in headfirst. Pull a Nike and just do it. If it helps, invite a good friend to come with you your first time. Many trans groups allow cispeeps to come too.
It was pretty nerve racking the first time, since everyone seemed to know one another, which only made me feel more out of place. Anyway, a few meet ups later, and I'm on friendly terms with most members. Taking a friend the first few times did help, definitely, but getting to know the ones on "top" first helped a bit, since they're the ones who basically explain everything and want to make sure everything is running smooth in their organization.