I'm not sure how I missed a few of your updates, because I am watching the thread, but anyway.... Congrats on making your FP+! Yay.
MNSSHP was awesome. I loved the parade, and I think that Hallowishes, is even better than regular Wishes. You often will read on these boards that one person will say that MNSSHP was packed, and another person who went the same night, will say it wasn't bad and not that crowded. I think it all depends on what you want to do. I went to a sold out party on 10/28/14, (I think it was) and I didn't think it was that bad. Main Street was crowded for the fireworks and parade, but it's always that way.... Some of the characters had very long lines, but I really was not interested in the meet and greets. I only met Jack Sparrow, and the wait was not that long. My priorities were the parade and fireworks, soaking up the atmosphere and riding rides. The Headless Horseman riding through to kick off the parade was cool. As far as wearing a costume, you will not feel out of place with whatever you decide to do. You will see people go all out, people who just wear a themed shirt, some that DisneyBound (that's what I did), and some who don't dress. I wore a red and white polka dot dress and my Minnie Ears.

I was comfy and I think I looked cute. I had a good time. Halloween is my favorite holiday.