I think 100% that games, especially handheld versions that differ completely in the gameplay should be split. It especially should happen now that games show their platform when searching. I can see if the game just has worse graphics or some things cut/changed around, but if it is a different kind of game or most of it is different it should be split. This is something that puts us behind other wiki sites I feel.
Considering I have been playing "retro" games since they were newly released, yes I do enjoy them. I seem to go back and forth between older and newer games quite often. Since being introduced to retroachievements.org by @jeff on the Bombcast I have been playing way more of them.
Which reminds me, if anyone else is into the retro achievements, shoot me a friends request, need to build up that leaderboard. I would only like to add people who just play the games though and not cheat their way to the achievements. Here is my profile.