Among the factors you mentioned that affected crossdressing, I think the internet was the biggest for me. I grew up before the internet, and as many other crossdressers of that era experienced, there was no outlet, no resource, for us to discuss what we were experiencing without outing ourselves and subjecting ourselves to ridicule, punishment, or forced treatment. Now we can have an open online presence of our femme identities while maintaining privacy of our real-life identities. This forum is great.
I've seen fashion trends change, sometimes significantly, over the decades. But I seem to be stuck in a prior era. When I was a child even before I started crossdressing (when I believe my brain locked in certain things that I was attracted to), women (both in person and magazine/catalog photos) wore deep red lipstick, accentuated the eyes, and wore high spike-heeled pumps. I still think those things are the epitome of a glamorous woman, and are an essential part of my dressup routine. Through the years, other things got locked in as well: eyelashes, short skirts, certain wig styles/colors, painted nails, jewelry, etc. My desire to pass is far outweighed by my desire to achieve a certain look that, in my eyes, perfects me in femme mode.
