i think you should definately do it chronologically. would have a much greater appreciation for games. and as far as the many nes games i think you should kind of do those chronologically also.  introduce a few of them at a time. dont want him to get to overwhelmed.

Just keep being yourself dude.  Keep playing the games you play and don't change anything.  Children always look up to their parents weather they realize it or not.  Just demonstrate an appreciation of every kind of video game and it will most likely wear off on him/her.

Yeah, I guess I don't want to turn my kid into some "science experiement" of the best way to introduce games.  But he is going to play NES games whether he wants to or not!

It is already affecting my gaming decisions though.  I bought chibi-robo for GC the other week... 

Hey man, first of all, congrats :)  Secondly, I'll share some of my experience with this same thing as to date.

My son is now five, and I started letting him tinker with an NES controller when he was around two.  Well, he had messed with them, but never really played anything.  When I showed him what certain buttons were for he got excited.  I told him the normal way a game is usually controlled is usually 'A' is to jump and 'B' is to hit the bad guys.  I think the directional thing came naturally to him... can't remember for sure.

When he really started getting into gaming though was when I put in a game of his favorite cartoon... TMNT.  That really got him hyped!  I showed him some other simple games too, like Sesame Street Countdown, which also became the first game he conquered by himself :)  I didn't single it out to just Nintendo either, even when he was getting started.  I put in Soul Calibur for the DreamCast, and that worked wonders for his self-esteem in gaming.  See, the cool thing about Soul Calibur is that you can suck at it, yet still get through it mashing buttons.  He went through damn near every character to see their endings.  He'd even kick my ass at it when we played two-players... and after awhile I was actually trying to beat him too! haha

Now he has an XBox in his room, and likes the PS2 in the living room too.  Sly Cooper is his favorite series by far.  He plays games every day.  One thing to keep in mind, is to only help them a little.  My son asked me for help WAY too often for awhile there, so I pretty much cut him off and said not to play the game if he didn't want to at least try.  Anyway, that's a bit off-topic, but I think it's good to let them try more for themselves than to help them all the time... just sometimes works I think.

He still plays NES along with the other systems too.  I think he gets that from seeing me play so often.  Remember, your kids want to be JUST LIKE YOU.  That's pretty much all you have to remember is to set an example by them seeing you play.  That's pretty much everything I've experienced in a nutshell.  Hope this helps you some man.

Oh, and try not to get mad at games in front of them... I'm dealing with him getting mad at games too easily now, and I could shoot myself in the foot for not thinking about that sooner :P