So, like makeup which I've experimented with (not wearing in the pictures) but not proficient with, I'm a bit intimidated thinking about hair ideas. I've been letting it grow out, and it's a decent length now. But since I haven't grown up learning things naturally, what are some ideas I could try as far as getting it cut/styling it a certain way/etc besides just brushing it? Though I do want to keep my length, as I've been trying to grow it out.

At this point, you could try parting it a bit more to one side or the other.  It's easy and cheap to do.

As far as what to ask your hair stylist (please, do go to a professional hair stylist to have it cut/styled), have you considered bangs?  The other thing would be to try some subtle highlights. 

I agree that going to a stylist is a good idea. Tell them you're trans and want a girl style. I was terrified abut this and so got my mum to come to the salon with me, so if you've got someone supportive that you trust, get them to go with you (or maybe you're less of a coward than me  )