These are all very good questions. I've thought about them some amount and discussed them with a few other people (both trans and cis) and I don't have satisfactory answers to any of them.

What I will do though is recommend a book: Whipping Girl by Julia Serano. Yes, it's written from the transfemme perspective and Julia makes no attempt to pretend to be anything other than a strongly binary trans woman, so you might worry (as I did before reading it) that it won't be relevant to you, or worse, that it will somehow say that your gender feelings are less valid than those of a strongly binary trans person. None of that is true. I love her analysis of transness, I feel very included (as a super masculine agender person), and really I just want more people to read this book because there are concepts and arguments in it that I'd never heard before and I don't understand why. It's a widely read and recommended book, so why the fuck have I never seen an internet discussion of the idea of subconscious sex? Or oppositional sexism and traditional sexism? Or the point that when we say a trans person "passes", it sounds like something the trans person does, not something society does to them, which is way more accurate? Or that our culture's hatred of femininity (especially in people assigned male at birth) is just straight up misogyny?

All in all, Serano's unwavering defense of femininity actually helped me embrace and understand my masculinity better. I no longer feel like I'm, well, "choosing the easy way". Masculinity isn't inherently better or easier or less contrived than femininity. It only looks that way because our culture is so deeply misogynistic, which is something we could conceivably change. Now you might (and actually I think you do) have slightly different issues than I do with regards to masculinity, but I would guess you'd still find something relevant to you in Whipping Girl.