As for what was being discussed last night, I know what people mean by entering contests with large/expensive grand prizes. I know I never tried entering Kia Ryou's contest because I knew I didn't have a chance and then her category prizes were around 50k or so. It's intimidating for myself. I know I could never win them. But that's me and I don't know many Gaian artists who participate in contests to ask their thoughts.
I'm picky, too. I tend to only enter contests with group categories with interesting characters or if I like the person running the contest and want to draw for them. I think all artists are picky and, of course, everyone wants to win.
I've been watching the Art Contest forum for a while now and I've seen many contests fail or have to be extended many times. I hope for my contest I can have plenty of gold or nice items to give away for each category. I've been trying to figure out how I should set mine up so it could at least be somewhat successful. I didn't know if a large grand prize would draw artists in, or a contest with a nice grand prize, but with very tempting category prizes.