My DS (now 8) had a Leapster when he was five & loved it. Then one year later he got a Nintendo DS & hasn't picked it up since. My DD then start to play with the Leapster & loved until Santa brought her very own pink DS and again, hasn't picked up the Leapster since. I think the Leapster is a great educational system, but I don't think it has the long term enjoyment factor that the DS has. The DS is definitely more expensive, but again may be the better investment as there are so many more games available. Just something to consider. I'm sure your child will enjoy which ever you chose.