To throw my two cents behind what's already been said, Costume Quest and Bastion are probably your best bets for new games, and Super Mario RPG, Chrono Trigger and Paper Mario for the Virtual Console.
If you don't mind soft-modding his Wii (which is a quite simple task; hard to screw up, but easy to fix if you somehow manage to anyway), drop some emulators on there and go for EarthBound, Final Fantasy III (6j), Illusion of Gaia, Secret of Mana...there's lots of good choices from that era.
Secret of Mana was my first RPG (well, closer to RPG than Zelda, anyway), and I got it in...I think 3rd grade, maybe 2nd. I'd tried playing Final Fantasy when I was four or five, but I couldn't understand what was going on at all. It wasn't until III/6j came out that I started understanding how "pure" JRPGs worked.