Personally, as someone who owned Pokemon Silver in 2000 and bought Pokemon HeartGold at launch this year, I found that I enjoyed the original GBC games more.
There have been changes made to the classification of move types since Pokemon Diamond & Pearl version which, personally, I just don't care for. But it is still Pokemon and it is pretty much the same as it was in the older games. The game does benefit from some newer features that were added in Ruby/Sapphire and Diamond/Pearl anyway, such as special abilities, weather effects (which aren't used as much), doubles battles and online trading/battles.
I would kind of have to agree with everyone else's opinions that you should wait and get Pokemon Black or White, however. They are brand new games in the series, and will be released sometime in March next year. They feature a whole new mess of monsters, but none of the previous 500-some pokemon are available in the game until after you beat the main story. Then you can catch some in-game, and trade other players for any favorites from the previous generations.
If your son REALLY wants some of the rarer pokemon like legendaries that can be obtained in Diamond/Pearl/Platinum or HeartGold/SoulSilver, then okay, you might just want to get him one of those games with those specific Pokemon in them, as they may be difficult to receive from other players. But honestly, I think he will be pretty happy with the new Pokemon - you're bound to find at least one monster you like among the new 150-some Pokemon!
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