I already have an iPad 1 and have had it for 5 months and am not a big gaming/video user, so in my case, the whole need to update to the iPad 2 issue was dead in the water-no point. But, if I were getting an iPad today never having had one: a $100 price difference might not matter so much. I would possibly just go for the latest version. But if it were like a $200 price difference, I would go for an earlier version with more storage-that sort of thing. That's just me. But in my personal experience, I'm moving right along quite unaffected with the release of the iPad 2. I mean, I think it's great that it's out-it needs to be. But I wouldn't be doing anything different with it than what I'm doing with my 5 month old iPad 1 that is still in rather pristine condition doing all the tasks I need it to do. Comes down to individual use. A lot of people for example don't even bother with an iPad and get for example an e-reader with basic web browsing and e-mail capability. Either way though, both the 1 and 2 are great and your son will enjoy either!