You make some very good points, and I agree with you. I don't think you're crazy for feeling bad, and I don't necessarily think it's down to female socialisation (men can empathise with others too, you know), it just means you're not hard-hearted or dead inside.

What I struggle with is what I might call compartmentalising my compassion. People who are suffering a genuine mental illness of course deserve our sympathy and support (within reason, of course), and you're right when you say that people enabling their delusions are only harming them in the long run.

It's a bit of a tired comparison now, but I like to think of this kind of thing as analogous to anorexia nervosa. Someone suffering from this serious (and often fatal) mental illness deserves compassion and support. People telling Tiffany that, wow, actually she is kinda fat, maybe going on a diet would make her feel better, would rightly be perceived as horrible monsters, even though it could be argued that this 'affirmation approach' would only really harm Tiffany and those in her immediate circle.

Where the wellspring of human kindness runs dry, however, is the with the chancers. The people who are adopting a transgender identity as a fast-pass for victimhood, and thus a fast-track route to getting whatever they want, because victims must be given what they want all the time (a separate issue).

If we return to our analogy of anorexia, the counterpart here would be the teenage girl who is reasonably mentally healthy, but loudly announces 'Oh my God I'm so faaaaat' so that her vacuous friends shower her in compliments. Or the social media compliment anglers. We've all got some in our friend group (or at least, used to) and we aren't expected to feel any great compassion for these narcissists.

The trouble, I find, is telling the difference, and treating the two groups accordingly. The saintly thing to do would be to give everyone the benefit of the doubt, and treat all people who claim to have a trans identity as if they are genuinely gender dysphoric (thus mentally ill) and deserving of support and compassion. Guaranteeing yourself a place in heaven, perhaps, but doing no favours to (particularly) women, girls or LGB people in this life.

The cynical thing to do would be the opposite: assume that they're all chancers who are trying to invade spaces, erase women, and indulge their slew of bizarre fetishes with non-consenting victims, thus deserving of basically little more than censure and opprobium.

I suppose it boils down to deciding which is the lesser of two evils: offending or upsetting trans people who are genuinely just trying to live their life in a way that makes them comfortable (the cynical approach), or allowing a few of the chancers 'in' in the hopes of trying to act as a genuine ally to those who might need it (the saintly approach).

I realise you didn't ask for an essay, I rather got carried away. Apologies.