2/3. THANK GOD NO. My first cosplay was Subaru Sumeragi in the red jacket and black hat. I think I have pictures of later iterations of it, when I got an actual hat and a wig, instead of just tucking my hair up under a black bucket hat that kind of had a large enough brim to be stiff enough to maybe look right. Thankfully I don't think I have pictures of my first three costumes, all of which were before I discovered wigs or makeup.
6. since I tend to avoid props, thankfully most of my costumes fit through doors and into seats and all that, but I think the away would have to go to either Odette!Tutu or Fuzuki-gami. Tutu of course because Jacqui and I made giant tutus, which give us a foot radius around us, and Fuzuki-gami because I always feel giant in it, with two kimono with tied obi, and a mask with horns and trailing decoration.
11. Most of my early ones, but that's more of an "oh god I hope pictures of this don't surface" embarrassment than anything. And even then, I was so happy at the time I was wearing them that I can't really get that embarrassed. I'm more embarrassed by the fact that I have a few costumes that are about 70% done that I just can't find the time or motivation to finish, oops.