I think that kids can have a lot of fun with math competitions even if they don't end up winning. At least, I enjoyed them as a kid! I have used Math Kangaroo problems in my DD's mathlab this year and all the kids enjoyed doing something different, stretching their brains and learning problem solving strategies. Usually the math competition problems are much more interesting than the daily practice stuff they get at school.

If they taught reading the way they teach math, kids would memorize lists of spelling words and never read any books!

Anyway, (rant over), what about Descartes' Cove? My DS loves that game. He needs me to explain stuff and help him but he is so motivated to try to figure stuff out. He will work on advanced stuff for an hour, but he'll balk at doing a page of an easy work book. I don't think it's just because I'm working with him...often he doesn't want to hear my explanation. He just wants to grab the pencil and go!