Hi Zack,
Welcome from another relative newbie here. It's a nice place, stick around.
I'm a bit older, but in a similar position of concern as far as work and stuff goes, and complicatedly I worry as much about losing my mom, dad and brother because of transition in much the same way you do. Sometimes I wake up with the nightmare of getting off the plane back home in South Africa and them rejecting me the moment I walk through the Arrivals gate.
Ultimately though I've had to realise that I have to be happy with myself or I'll just end up hating them for it, so this year I've made the decision, promise and resolution to transition in earnest - I've done my part by providing information, by taking things slow and by "making sure". The people who truly love and value me will hopefully find it within themselves to accept me as I'm meant to be.
Try to be true to yourself, or you'll always regret and resent it.
Lots of Luck and Love,
Simone