I would look at the child personally and see what he'd be more comfortable with. My first leappad definately covers pre-K and a little kindergarten (VERY little). Leappad itself is geared more towards kindergarten on up.
We had both; I think we got the "My First" when my son was about 2.5 . He loved having the stories of all his favorite characters (Thomas, Bob the Builder, Dora... all the preschool set). He was a smart 2.5 year old and within a year mastered all the books. I think we found a Leapster when he was 3 at the thrift store (I find them there all the time, usually around $5 or less). We bought him that, and while he enjoyed it, the books he really wanted to do were above his level of reading capabilities. We still bought him the books he wanted, there was certainly nothing in them that were offensive. I figured he could play the 3rd grade books just fine, if he wanted to. He learned musical instruments and geography just fine, but the advanced levels really turned him off and now it mainly sits in his closet. He really appreciates the Leapster more than the Leappad.
My daughter will be 2 this August. She is so different than her brother as a youngster and really won't appreciate having to sit still for a long span to play the Leappad. I think she will get his old set for Christmas this year. I am counting on the characters to be a big attraction in getting her to sit still and play the games. She also needs more of the basic skills work than my son did at this age... colors, shapes, counting...all the pre-K stuff. My First Leappad is perfect for that.
My vote would be for a just turned 3 year old, get him a My First Leappad set. You can find good deals on used ones on ebay, at Thriftstores, and every now and then
Walmart has a package deal (every Black Friday for sure). If he knows most of the basic pre-K stuff, I'd skip the My First Leappad series completely. My son likes his leapster better than the leappad, too... but if you want to avoid the electronic stuff, go with the leappad, but be wary for a limited book selection right away.
Either way, I'd buy him the entire Leapfrog DVD Library. I swear those movies helped my son read and learn all his letters. I think there are 5 or 6 of them... letter factory, word factory, code word factory, storybook factory, and math circus. I think I named them all. I saw a box set at costco last Christmas that made them fairly cheap, but I haven't seen it since. Normally they are $10 a movie new at Walmart.
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