Hiya
I'm in the UK so can't give any worthwhile advice about transitioning in the US.
I can however offer advice & support on the rest. First things first, questioning your gender identity doesn't mean you're any more crazy than the average human being (lets face it, there's no such thing as a completely sane person, lol).
Coming out to family is a minefield, some people start out accepting then become uncooperative/hostile & revert back to accepting (Yes i'm talking about you mummy). When a family member comes out as trans those close to the transperson sometimes go through the five stages of grief as they feel like the person they knew is gone, I suggest reading about this online to prepare yourself.
It's not fair to judge people on how they act during this stage as it's takes many of us years/decades to come to terms with this in ourselves so those close to you will also need time to come to terms.
If I was in your shoes i'd have a few psych visits before disclosing to your family, it's best to be certain before you let the genie out of the bottle as he's a bugger to get back in.
Best wishes
