I'm somewhat familiar for the reason behind November:

http://www.sankakucomplex.com/2010/11/18/vippers-vs-fujoshi/

Does anyone have any idea why the heck May is the way it is?

May has been successfully dealt with

Added the chargeman_ken! tag. That's the source of May. I honestly don't know any more - it's a meme on Nico.

Thanks, HydroKirby.
He is one of bad guys appearing on episode 25. You can search this guy by using Pixiv tag search: 'これから毎日家を焼こうぜ?' ('Kore kara Mainichi Ie wo Yakouze?')

and september is? Hoatio Caine? :)

wtf happened in May and November?!