Thank you! That's very helpful, seriously. Those photos were like the first or second (maybe third? I don't really remember) time ever trying anything with makeup, so I'm well aware that my makeup game needs plenty of work. Stuff like contouring is definitely something I'll look into - also eyeliner. I haven't quite got the hang of the steady hand yet, I guess, for anything more complicated that what I did there, but practice! That'll help, and I'll try cat eyes (presumably not by basing them on my cat's eyes, mind). On eyebrows - once I'm ready to go full time I'm going to do them (or get my sister to do them, she's got herself qualified as some variety of makeup artist recently, and I imagine she would very much enjoy inflicting pain on me with tweezers). It's just when I'm still going around as a guy most of the time I guess it would be pretty hard to hide shaped eyebrows. But someday, hopefully not to far away, and I'll bear in mind the high arch suggestion. I'm not particularly good with lips, and again the steadiness of the hand with lipliner is an issue, and even then lipstick seems to go very much everywhere, so. I've read that using a small brush to apply lipstick can help with that? But again, practice! There'll be plenty of that. I want to absolutely nail a good look that I can stick with and work with even just as somewhere to eventually progress from, if at all possible. I tend to buy / wear dresses and skirts that are at least a bit flippy or flared to help with shape. My measurements are okay - 34-26-34 - but my hips tend to look way too small in relation to my shoulders, so. Advice definitely noted re: what sort of tops would be more flattering. Get paid at the weekend so maybe a bit of shopping. Posture is an issue for me - I tend to slouch quite a lot compared to most people, mostly from spending many years trying to get around without people bothering me. I've been looking into good ways to help with that.
Also I am going to get my hair cut properly at some point - probably going to look to go with a fringe to help cover up a bit of brow bossing, and then have the rest just down and framing my face and I'll just straighten in. I've got that down to a relatively fine art, at least.
Anyway, thank you again! Very helpful.