Ah, good, another parent who is as crazy as myself . I bought my son his Leapster for his 2nd birthday, and it has been his favorite toy ever since. He is now 2 years and 9 months old, and has mastered so much already!

Here are my recommendations:

You might consider getting your son the Letter Factory. This cartridge is discontinued by LeapFrog out of some strange reason, but you can get it on ebay for example. My son knew all his letters both by name and the sound that they make by about 2 years and 1 month, and the Letter Factory cartridge was one of the reasons. It is mainly a video, but then it has an interactive multiple choice quiz for letter recognition.

The Backyardigans cartridge is also a fairly simple early one.

I also highly recommend Mr. Pencil Draw and Write, which is a slightly more sophisticated drawing software package than Color Coral. Among other things it teaches about color mixing (yellow + blue = green), and there is a simple game on there that has one pick from multiple choices what the program is drawing before the drawing is complete.

Also several cartridges have a mixture of simple and difficult games, for example, Dora's Wildlife Adventure has a fairly simple matching game where you uncover cards and find two that match (colors, shapes, letters, etc matching), but the same cartridge has several more chellanging features. My son has had no problem picking and choosing what he plays on different cartridges, and sometimes he plays for a while with something that he finds easy, and at other times he keeps trying features that are really beyond his current level (and while he does get very frustrated with those sometimes, after a while he estonishes me with which features he has learned).

At 2 years and 9 months old, after 9 months of owning Leapster, we have come to a point where I just consider any cartridge that is rated for age 4+  to be within my son's possibilites. He may not master all of it but he can interact with enough features and learns a tremendous amount from them. We own 16 cartridges so far. I have already responded to another person's request for recommendations for games in the Leapster 2 forum on this website, so you may want to check out what I wrote there also (I commented on more games there).

All the best!

Joanna