My DS bought the black Star Wars Leapster 2 with his own $ several months ago. The downloadable content is like two games, so nothing spectacular. The online learning path monitoring is cool, but I haven't looked at his in a while. Really it doesn't do much more than the old Leapster except look a little cooler.
Our scenario was a little different in that my DS is dying for a Nintendo DS...and I'd really like him to keep playing his educational Leapster games for just a bit longer, so I kind of talked him into the cool looking Leapster 2 over saving longer for a DS. Especially since he has so many age-appropriate cartridges that still keep his interest.
So selling him on the "older kid looking" cool black Leapster did work and he's playing it and enjoying it, however he's going to ask Santa for a DS, and I assume that once he gets his DS he will no longer play his Leapster.
Oh, and a funny thing is that the built-in games are slightly different...and my DS still will pick up his old Leapster to play sometimes! And he also wants my DH to play the other Leapster at the same time...I think to pretend to be playing together as if they were DS's - LOL!
I don't know if my rambling helps at all! Best of luck!