Grandmaster: yes, they should. Clothing is a big part of group identification. I don’t like it, but it’s a fact. Even the halacha provides for it with regulations on how big your kipa has to be, etc.
Re the choylem: The Mislol, written by a grandson of the Tosfos Yom Tov. (I confess that it’s the only dikduk sefer that I’ve actually learned through a large section) and a psak from my rebbi who is a baal kria and reads with an Oh cholem, as does his rebbi, Rav Yisroel Belsky.
rescue37: technically, yes. Simchas Torah is also technically the second day of shmini atzeres.