i would say consider removing compound not italy if you want to test drive jailbreak. Which, btw, is indeed a classic and a great cs map to play!

contra is not a very popular map either, pub or ladders, it's just such a sad looking map

as for a custom to official ratio, I wouldn't worry about it. If the maps are liked you will get players on.

if you are looking for an aim map I would recommend cb_training I think that's what it's called. It's a great aim map and perfect for multiple opponents.

and if you want to see if a map might be well received, search for servers playing it.