Oh boy that was a long list of items for Cosplay... thanks for the very thorough feedback!
It's because I care.

(seriously. I don't think I'd have that much to say if I was apathetic) Masquerade has often been my favorite thing in conventions, and I want that back.
Edit:
I forgot about this one because I don't really attend it anymore... so mine is based off of past years and what I hear. From what I've heard, it hasn't changed.
Cosplay Spectacular
- I never particularly cared for how skits and certain walk-ons were mixed. I think the ones showing off their costumes & singing should be part of a separate event. I'm talking the individual ones (not the group ones.) I used to go for the skits and only the skits. I'm ok with singing if it is part of a skit but I don't think they should allow "I think I can sing so I wanna show off" individuals. Honestly, they should be taking part in karaoke not masquerade. Or maybe Stage Zero.
- At least make the costume thing a separate event... it doesn't do well on such as large stage and I think would do better in more of a cat-walk/fashion show setting. Have these people sign up for a "Cosplay Fashion show" instead. Plus, it gives you another event at fanime.
- Judging: I have no first hand experience with this but I've heard judging is rigged & biased. I think it should either be done by an independent party or an audience vote. We don't need to know the results right away; the fact that they already know who won just shortly after the show ends just screams "fake." We the audience aren't dumb and know the results aren't true.
- You know what... make the results a separate thing. If it isn't a audience vote, make it into a panel or event where it is one of those over the top judging shows. Where the judges have to explain what is great or bad about a skit.
I'm okay with splitting up the event. An idea I had was a cosplay fashion show on Stage Zero each day, and the winners of each day could show up at some point during Cosplay Spectacular and walk-on while the MC talks about the awesome parts of their costume that's why they won. 'Cause being honest, as a crazy craftsmanship cosplayer, that's what I want people to know about. However, that wouldn't work if, like this year, people don't want to do skits.
Also, I don't think singing skits have been allowed since at least 2009 (I seem to recall some live audio in 2008?). The rule's always been pre-recorded audio. For some reason, even though it was explicitly against the rules, some skits were allowed to do so anyway. Don't ask me why.
On your judging suggestions though - As somebody who competes and does attend these things, I'm certain that what you hear about judging is hearsay. There is a separate panel doing judging. I have a lot of problems with Cosplay Spectacular this year, and the judging is not one of them. Masquerade staff does not judge these things - it's an outside panel, although they do often repeat (I think Wayne Kaa's local). Wayne Kaa's from ACparadise, I believe, and he's been judging at least since 2009 when I was competing. This year, the cosplay GOH was one of the judges (as it should be). I don't have any issue with the panel.
Additionally, one reason judging doesn't take as long as you might expect is because all the workmanship judging is done outside of the main show. It's not like the judges are doing their craftsmanship evaluation when the competitor is onstage. If the judges have a sheet where they score performances as they perform, judging is a simple matter of tallying points. And announcing in the same event makes sense because that way you have the competitors in their winning costumes for publicity photos. And this is still a costume competition, even if skits are involved, so that part should absolutely not go away.
I do like the judges saying when the awards are given why they gave that award, and I know in years I've competed, they often have. I did have to duck out for the announcement of the winners this year, so I don't know if they did or didn't. I just heard about who won, and nobody who won surprised me.
An audience vote beyond a single crowd favorite winner should never occur in a convention of Fanime's size. Then the winners would be, in many cases, a case of what anime or game is popular at the time, and dramatic skits wouldn't be given a fair shot.