you need to decide what you need to do for yourself. forget what your family wants, forget what you're told is easiest. this isn't about what's expected or what's easiest, in fact, you're doing the unexpected and what's going to be hard.
i never told my parents that i asked for a T letter, and i didn't tell them that i got one. i haven't told them that i've started T. i can't say it's the right decision, but it's what i've had to do for myself to get my life moving in the right direction - to start taking steps towards achieving completeness and happiness and peace within myself. granted, it's come with the guilt and fear of what they'll think when i do tell them, but i know i made the right choice to pursue this for myself. i needed to be the adult that i am and decide to make this life changing decision without relying on my parents' judgements - or anyone else's for that matter. it's important to remember that this is about what you need, not what they need.
that being said, you should always take into consideration the thoughts of the people closest to you, as they really do care about you and despite the hurtful things that can come out, they're looking out for you. when i came out as trans to my mom, she said some pretty stinging things, but i know they came not from trans-phobia, but from being afraid for my well being.
i can really relate to some of what you're going through. i can't tell you what you should or shouldn't do, and i can't give you any words of wisdom, really. just...think carefully before you make any decisions. and you know what? maybe expressing your desire with your therapist might be a good idea, and mention your reservations about your parents. that's what therapists get paid the big bucks for.
as for the dysphoria, the bad days and the blues, i hear you. i bind well myself, but i have an immense amount of difficulty passing effectively 99% of the time and i certainly have issues with my anatomy (and the lack of). i get sad and moody and everything in there, but i have to take solace in the thought that this is who i am and who i want to be. everytime i get a "she", i have hurdle the initial disappointment and keep on being myself. they saw me as "she", but i see me as HE.