Sunday OT Post: Yes, I know it isn't Sunday...
I meant to post this last night, but got rather involved in Guild Wars 2 instead so I completely forgot. For years now I've been meaning to get back into board games. As a teenager I played some war games that I absolutely loved. Now that my eldest is near 13 I've been hoping to get back into it and - obviously - involve him.
Last night my son and I played our first game of Mage Knight. (Associate link below. ;) It was an incredibly cool, but complex game. It took about 2 hours of setup to get started and my son was definitely running low on patience.
But then something magical happened. We both went form struggling to "get it" to, well, I still don't think we get it completely, but we got to a point where we could actually play, and his face lit up, I got excited, it was just fun as hell.
That being said, while we plan on playing again, I'm curious what games folks would recommend that are a bit simpler. If Monopoly has a skill rating of 1, Mage Knight is somewhere at 100. That's cool and all, but I'm hoping for some middle ground in terms of complexity.
Any suggestions? I'll point out that no one else in the family is that interested, so 2-player support is kind of required. Nuclear War is already on my list to pick up.

Wil Wheaton (yes the Star Trek guy) started this video blog about a year or so ago. He has some of his old cast mates, writers, friends..etc on and they show how to play one or more different board games. It's actually kinda cool.
It will give you a good idea of whats out there and if you and your kids might like it. Plus kinda funny sometimes.
http://www.worldofmunchkin.com/game/
www.catan.com
Starts out "Easy" but can get more complex.
Goes well with kids and/or beer.
(Yes, I went cheap on shipping.. :-p )
Another place to check out board games is Wired's geekdad blog (wired.com/geekdad). They also showcase a lot of kickstarter board games which look interesting.
Right now my kids are learning Candy Land, not quite what you are looking for, if Monopoly is 1, Candy Land is -27, but I still remember having fun with it when I was a kid.
http://www.reuters.com/article/2012/01/31/us-candy...
The only problem is a father can't play it with his son because the father is confronted with the possibility of stabbing his son in the back.
"Ticket to Ride" is another railroad game, but with preset rails (no crayons).
I see you on there Ray every now and then (my player name is Webstalkers). Maybe we can get a multiplayer session going sometime.
boardgamegeek.com is the meta site for boardgaming, but a UI nightmare
I presenting a bunch below in three categories. All are either for or great with 2 players. Basically, look at the picture of the box to see if you would like the theme. There is sci-fi, dark fantasy, realism, "old world" abstract, high fantasy, etc.
Catan is not good for 2p. Munchkin is ok for about 10-15 minutes, it's like a 2 on your scale above.
One thing to note is that a lot of games are either "living" in that they have regular expansion installments or they have one or two expansions to add more to the game, such as Mage Knight's new expansion. X-wing is the only one that needs an expansions that I've listed below.
Player vs. player (eliminating each other) -
Android Netrunner (love, love, love this game),
Star Wars X-Wing miniatures game (get the starter and one of each expansion) (love, love, love this game),
Claustrophobia (if you are ok with demon theme),
Blood Bowl team manager,
Memoir '44.
Co-op - (the first three are very similar)
Pandemic
,Flashpoint fire rescue
,Defenders of the Realm.
Lord of the Rings, the card game, like Android Netrunner encourage you to buy expansions.
Dungeons and Dragons Legends of Drizzt board game.
Player vs. player, but not really direct conflict:
San Juan,
Thebes,
Galaxy Trucker,
Ticket to Ride: Nordic Countries,
Tikal,
Tobago,
Alhambra