I have different sorts of family. I just came out to my brother and his wife last night - it's actually *more* difficult in a letter, watching them read it, watching their expressions... And in the end, they're totally supportive. They are liberal and my SIL has someone in the (very extended) family who transitioned.
The question is... when do I tell the people I really fear to tell? There's a reason I chose my brother and SIL first - you're never sure what to expect, but I at least had a lot of hope. There are reasons I feel like I need to tell people earlier in my family... and I really like to come out and be out about it, but the family situation is complex.
My sister and her husband will be more difficult. I don't fear my sister, but my BIL definitely has the chance of rejecting it and of telling the world (which includes my BIL on the other side - who he works with). Regardless, they may be the last I tell. My wife's side also will be much more difficult. Her parents I should tell first, but I don't know how to approach them (I doubt they'll understand). One of her sisters is more liberal... I would tell her first - but her SO works with me. The rest are more likely to go nuts over it.
How do you tell people like this? I have a personal, touching letter... but it's difficult. I also won't be able to stick around while they read for some of these people (my sister, yes... that liberal SIL and my work friend, yes).
In any case... the rest are all waiting until after my next appointment.