The following are my all time favorite maps from years of playing VSH:
military area /military zone (in general, cause there is like 50 versions, good for many classes)
dust showdown (fav sniper map)
egyptspot (2nd fav sniper map)
oh multimaps (good for many classes, the variety keeps things fresh)
minegay (fav engie and heavy map, but good for pyro, soldier and demo too)
2fortdesk (2nd fav engie map, 2nd fav soldier map)
skyhigh resort (good for engie and demo)
warebloom (good for demos and engies, many classes)
crevice (good for many classes)
castle siege (fav soldier map, good for many classes)
There is also one map I can't remember the name of, but I always had fun in it. I drew a picture of it:
https://i.imgur.com/JqlqZSE.png