This is a very good post and nearly all the replies here are illustrating the exact issue that Bob has, which is an inability to engage in the dialectic between these two perspectives without indignation as a defense against guilt.
Most people, including myself, are more Bob than Alice, but I’ve had a much easier time integrating my inner Alice and engaging with Alices I meet because I rarely, if ever, feel guilt about anything. Strong guilt increases the anticipated costs of positive self-change, and makes people strengthen defense mechanisms that boil down to “I don’t owe anyone anything!” to avoid confronting that cost. Ironically this creates people who think they’re not predisposed towards guilt, but absolutely are.
Don’t get me wrong, Bobs often have pretty understandable reasons to be the way they are. A lot of Bobs got out of religious groups that were really aggressive with the guilting. But understandable reasons to be in an undesirable state does not increase the desirability of that state!
Having met a number of Alices, I think they need to invest more in the consequences of the manner in which they try to get other people to improve. I understand their frustration but the aggressiveness is really so counterproductive and just makes Bobs even worse. Bobs unfortunately need to be treated with kid gloves to get them to improve without feeling in danger of self-guilt-torture.
Speaking as someone who’s been on hormones for 4 years and considered myself trans for 5, this is probably the majority of detransitions (insofar as they can be considered “de”). Many of my friends have detransitioned without any regret for taking hormones (or continued hormones but decided to socially detransition, etc), and they usually remain fairly integrated with trans friends, having enough trans experience to “get it” and be an honorary trans no matter what. Like OP said, cultural integration is pretty sufficient to remain in trans communities even if you’re “cis”.
I think there’s a very common perspective that having a non-cis-typical body is a horrible disfigurement and that’s why vocally regretful detransitioners are given such a large platform in media (despite their grievances being about the same or less as a trans person forced through natal puberty). Most trans people come to peace with having a non-cis-typical body in the process of being trans, so in the case of detransition it’s less horrible regret and more like becoming a trans person in the other direction. Notably the most vocally regretful detransitioners are formerly of the type of trans person who loathes being trans and gatekeeps it strictly as a reified medical condition which is to be Treated with hormones.