I'm curious as to opinions on this... so here is the scenario...
(Sorry if this phrased awkwardly, I'm trying to be succinct without leaving anything out that may matter to the decision.)
I am only really just getting started in this process, and at the earliest (assuming I maintain the courage) I probably won't be starting HRT until at least the beginning of next year, as I need to drop more weight(between evacuating tomorrow from a hurricane stress plus the upcoming holidays, that will be a challenge). But meanwhile, I'm starting to feel isolated even around family, walking around with this hanging over my head. My living situation is awkward, as I am 35 but had to move in with my dad a few years ago. The household also consists of my step mother, a semi-disabled adult step brother, and high school age sister.
So, I've been really feeling the urge to come out and tell my dad about what I'm going through. He's in his 70s and on the conservative side(religious but not enough to go to church every Sunday), though he is also a psychiatrist (as is my step mother) who has most certainly dealt with a number of transgender patients, and a compassionate if reserved person. I think it might be painful for him to hear, but I don't expect a blatantly negative response. Though I do also fear that his work may have him predisposed to a somewhat dire view of being transgender, as he primarily deals with extreme cases with crisis centers and major psych wards. (In other words, he sees the worst of the worst.) He is also already aware of a few incidents as a kid (caught cross dressing :x), so he'll at least have to admit it didn't just suddenly come out of nowhere.
So considering I'm still probably half a year out from doing anything major like HRT, would it be premature to come out to him? I have a fear that I'll tell him, things will get awkward (which is quite likely even though I picture him being accepting, he gets flustered easily when my sister pushes his buttons by joking about being a lesbian), and then I'll chicken out and not go through with anything on top of it. That would be unbearable to me. Also, I am moving out summer of next year regardless, so if I were to wait and there was intense awkwardness it at least wouldn't be for long. On the other hand, if I tell him early he may be willing to help me financially with things like therapy, but I don't want to let money be my motivation for telling him.
I'm really torn on this, because emotionally I feel the need to tell someone but intellectually I know that nothing can be gained (setting aside therapy payments) from doing it this early (and much can be lost, even if it just a normal day to day interaction).
(To give an idea how much this is weighing on me, I'm evacuating from Hurricane Irma 8 am tomorrow morning but I'm awake posting this.

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