Someone earlier in the thread said around 60 or something. You have to remember that most kids would pick their in-state if they got in just for tuition purposes (unless it's somewhere like Penn whose in-state is expensive), so the OOS list for most schools moves quite a bit. I went to one school where they offered 80 spots and only 12 accepted and they went down into the 100s on the waitlist. Virginia probably won't be as many since it's OOS tuition is on the cheaper side. I'd expect at least 30, probably more.
Last year, I was wait listed at VMRCVM and accepted nowhere else. In terms of if it gets easier... I was super bummed the first week but then latched onto the idea that maybe I was #1 on the waitlist. You think about it less and less until April comes around. When I asked, I realized that there was no way I was getting in (#20). All I could do at that point is start working on improving my application for next year. However, if I had offers at other schools I'm sure I would have been more stressed. So I would say it gets easier and then when April comes it either gets easy or hard again.