I think the system works as intended, to a large degree. As a past winner in the beginner category, I did basically what Bill laid out--I entered my models in the beginner contest in part because I relatively recently took the hobby back up again (my winning entry was my 5th build since coming back) and in part because I wanted to gain a bit of confidence. Having "graduated," I'll keep entering my builds in the advanced category contest from time to time. Even if I don't win ever again, it's still going to be fun and challenging!