So I found a pretty annoying thing when I was going through some of my old eroge, Virgin Roster just doesn't work. By that I mean I mount it with Daemon, I double click on the shortcut, there's a brief spin and nothing else happens. If I click on it through Daemon Tools I go to the start screen where it asks if I want to Play, Uninstall, Reinstall etc. I click on play, same as before nothing happens.
Strangely enough this so far hasn't happened with the other games, i.e. Prison Battleship.