Thanks so much for all the thoughts, suggestions, and kind words, everyone! I actually felt a little better just writing all of that down and sharing it, and reading through the replies has helped even more. I'm so glad I decided to start being more active on the forums here!
I guess to give a little more context on me and my life, I grew up in a relatively homophobic and transphobic area, and many of my friends that were gay faced refusal of service, verbal harassment, and on rarer occasions, physical violence when out in public. None of them were the type to start or escalate anything, so I think it was mostly just a hand full of hateful and violent people feeling free to do as they pleased. I do live in a different and generally much more accepting part of the country now, and times have changed, so I know my risk of those kinds of experiences is much lower, but it's still hard to shake that kind of baggage

I've also had self-confidence / self-image problems since I was little, and I'm generally averse to risk and change, and prone to anxiety and fear of uncertainty. So regardless of what steps I end up taking, just being trans in the first place is pretty much a perfect storm of most of the other things that I already struggle with

I'm a lot more sure of things on the medical side, as I know which things have bothered me in private for over a decade, and what I wanted to change even if I never ended up going out in public.
The social side of things is more challenging for me though. My attitude on being gendered male varies between total indifference and total hate. My mannerisms in private tend to vary with my mood as well - in general, the more energetic and emotional I am (happiness, sadness, anger, love, and contentment all work!), the more feminine I tend to feel and behave; but the more tired, or dull, or numb I feel, the more I tend to feel and act more neutral or slightly masculine. I don't consciously put effort into any of that, it just seems to happen automatically and has been that way for years, though I am more likely to unintentionally slip into 'girl mode' in public since being on HRT for a while.
On a good day, I would be super happy being out in public and on those days having to present as male feels very confining and upsetting, but on the more dull/numb days, trying to use my more feminine mannerisms feels more like extra effort to blend in rather than a natural expression of how I feel. It's those variations in attitude and behavior that tend to fill me with the most doubts. I've also been having a lot more stressful dreams lately about being closeted, or being outed before I'm ready, or just feeling uncertain of myself and my identity, which doesn't help matters either.
One thing my therapist suggested that helped me figure some things out at least, and that might be helpful for others as well, was to pretend that I knew for certain that I would never pass no matter what I did, but that most people would at least be reasonably polite, and the worst I would encounter would be avoidance, odd looks, and occasional verbal harassment. If I knew all of that for certain, would it change my plans? So far I've stuck to doing things where that kind of future wouldn't make any difference.
I do like Kathy's and Dena's suggestion of going somewhere for a day where I wouldn't likely be recognized and seeing how I feel about being out publicly as female. I don't feel ready for that quite yet, but I think it's something I'd want to start experimenting with in the next few months and see how it goes. Given my tendency to naturally vary in expression based on my mood, I think it's especially important to try going out on some of my more dull/numb days and see how I feel about it. Who knows, maybe I'll just end up rocking the tomboy look on days like that and loving it!
On the topic of going out publicly, I do have kind of a fun story from around the 2 month mark. I had a couple days where I was out shopping in different neighborhoods than usual, and I kept getting male fail! It was exciting, and confusing, and scary all at the same time. I wasn't upset by it, but more just confused at how other people were already seeing a woman that I have a hard time finding in the mirror, and feeling like it was too much too soon and I just wasn't ready yet. I do have longer hair, but I was in baggy male clothing and hadn't even done the best job shaving

I do think I might have accidentally been slipping into some of my more feminine mannerisms and to a lesser extent my voice, and maybe that was enough to push me over the edge? I didn't get any 'sir's and I kept getting 'ma'am' and 'dear' from multiple people, including throughout a few of 10+ minute conversations! Maybe they just took an initial guess and rolled with it because I didn't complain? Either way, I certainly wasn't going to 'correct' anyone