Italy is full quite a lot, it just depends on when you go on .__.my 2 cents, Rotation server would be cool for you guys, if anything I could see this happening with your HS one as its really hard to fill, I was sitting with RIC almost all night yesterday and nobody hopped on. Italy never fully fills, Office does decent. Your Jail server is not on Gameme listed so as far as ranking goes it more of a leisure server imo like TF2 quakelive server which is why when I help cs fill i don't prioritize it and also you need a good group apparently to jail. I'd vote maybe converting hs to rotation and adding hs as an option on it so its not really gone, win win.
Well that's what this is here for! To get an insight on what the players want. The Highschool server is going to be tough to get back up there because not a lot of pubs look for that kind of map when playing CS:S.

Why not use highschool as a rotation server? Not a complete rotation but partial. Make it go like
highschool
italy
highschool
office
highschool
de_dust2
highschool
etc...
Make the rotation speeds around 20 mins each so each map will be quick, but highschool will still be in there a lot!
Seems likely people would just hop off into the filled servers when the map switches to something we already have a server for.
I wouldn't do modded maps, aside from Highschool. New players don't like being stuck downloading a map; they want to play. I'd replace Dust2 with the original Dust and Italy with.... say.... Nuke! Or Assault! In fact, CS Assault is one of my favorite maps aside from Italy....
A rotation server has been done more times than I can count. They usually start off pretty strong, people fill it without being asked and everything's dandy. It rises in rank and people will think it will become a success. Then, people stop playing the server because they filled their craving for the month, and go back to playing any of our other (and in my opinion, much better) servers that only have one map that has a consistent group of people that play on it.
When people from our community stop making a concerted effort to actually play on that server for months on end to build up a following of non-community members, then that server will almost always fail. This trend has repeated itself for years and years on end. Why do you think the only rotation server we run is jail? Because other rotations just don't work for us. New servers take far more time and resources than most people think to start up, and when a server is empty 90% of the time, and the other 10% it's 7 eGO members in the server, 2 of which are spectating to "fill" it, there is really no good reason to keep it around and waste the server resources to support it.
Source: I've been here for a really long time.
I'm talking about on the rotation server. Instead of putting Dust2 in a rotation server, since we already have it, I'd put the regular Dust map in there instead.