A few years ago I managed to put a windows game server (rFactor) working in a linux VPS and it worked pretty well. At the time I used X2Go to remotely control it.

Recently I've made some experiences with a VB6 application in a linux desktop (using VirtualBox) and it worked too. I would start with this approach to solve wine/vb6 dependencies, and then move to a server (without X) and X2Go.