Hi, Troy.
I know it sounds pat and simplistic, but people tend to do things when they are ready. Unless you get pushed into coming out, you'll have the rather dubious opportunity to find your own...breaking point. The point at which you cannot stand it anymore and you simply must come out and risk the consequences. Many (perhaps most) of us fight it and fight it until we cannot fight it anymore. And then, sometimes, we make hasty decisions.
Seems to me you're playing it smart--you're aware, you're not in denial, you're seeking support and community, you're laying the groundwork for coming out to your family.
You can lessen your fear and apprehension by feeling in control, or as in control as you can be in a situation like this. So education, support, and preparation can be very important.
Do you know how your family members feel about trans issues? You can often find out a great deal about people's attitudes without ever coming out yourself. If you find sympathy and an enlightened attitude, even from one family member, that can go a long way toward mitigating the fear. Perhaps once the fear or pain of not coming out outweighs the fear of coming out, you can take measured steps to come out to one person.
At least you're not doing it the way I did it. I denied and delayed for so long that when I fully came out and admitted that I already WAS a man, I had very little control and a huge amount of fear. I spent nearly two years mostly just putting out fires and reacting to my situation. Only recently have I started to feel like I have some control over my own life. And only very recently have I started to see that even when it boiled down to "transition or die," I CHOSE to transition so I wouldn't die.
Having choices, and knowing that you have choices, makes a big difference.
