Well, hun, first off, you look very feminine in either mode, so if being pretty is your goal, count yourself very fortunate, you ARE pretty already!
From my own perspective, I grew my hair out as soon as I ran away from home as a teen and let it grow as long as it would grow, and rocked that 'southern rocker' look as a 'dude'. So, I never wore a wig when I made the switch, but I can only guess that wearing it would have made me more dysphoric, not less. I know that when I stuffed my bra, the same thing happened, I felt phony, and I 'lost' that lovin' feeling, so to speak, lol..
You seem to be doing all you can do to make things better for yourself already, and yes, my goodness, HRT was the fuel that my brain needed to 'believe' I was a girl, even though I have no Y chromosome, lol. Once I was on E, everything about my internal confusion became crystal clear. I can only guess that for an MtF, the same must be true, but that is only my guess.
I was with a woman that wasn't into the reality that I was born female, so I tried desperately to delay everything my doctors told me I needed to do. I delayed HRT, then delayed dressing in front of her, everything. I was being gendered female after about 6 months of HRT while wearing boy clothes and having had no facial hair removal, but I still waited until after I broke up with my gal until I went full time. My point? Once you get on HRT, somebody as naturally feminine looking as yourself is likely to find herself being seen as female no matter what you wear, no matter how long your hair. My guess is that your transition train is going to take off from the station at a crawl and end up as a runaway train very quickly, so to answer your question about what to do to prepare yourself, my answer would be to start clearing the way for a fast track to full time. Once you get on E and T blockers, you are going to be unstoppable...
Yes, transition is about more than 'passing', and there seems to always be more that can, and should, be done. But gosh, for some it starts with a bang, and then tapers off, for others, it starts slow, then builds up speed and momentum. My guess is that you will be the first type..
Hope this helps..
:-) MissyG