Aww ... you look so pretty
I think you will look GREAT with your natural hair! So glad to hear you're going for it. Just some thoughts on your parents and transitioning:
I do wish your parents were more supportive of your transitioning. Maybe the fact that your mom had one failure at trying to transition plus she watched you pull back too, makes her feel pessimistic now. But I also bet your gut feeling is right about her being conditioned to have straight hair. And men are conditioned to think of longer hair as more feminine. But it's the younger generation (yours, in particular) that seems to have a more enlightened view about going natural. And you are COMPLETELY on the right track by embracing your beautiful, natural kinks and/or curls!
You're obviously more dedicated to transitioning than you were the last time. You've just talked about all the research you've done, plus you're here posting for support! And no, you don't have to cut it all off at once. That's totally up to you. There's no question that not everyone is accepting of natural hair YET, but you will probably inspire countless other young and older women to go natural - just wait and see
I consider you a trail-blazer and a leader for setting your curls/coils free. And the best part of it is that you will likely discover just how much you love the hair you naturally have