I've been following this one for a while, and thought I'd chime in.
I'll get the dislikes out first:
-Hard to meet new people in general. All in all it's a very 'from there' kind of place, not necessarily from the surrounding area, but from Wisco. I'm 27, and it seems that anybody here that's my age is either from here, or moved here with their former college friends, and are quite content with knowing 6 people.
-People LOVE to get married here. They almost seem to yearn for it. That's not necessarily a bad thing, but it is when you're single, like to go out and do things, and everyone is too busy sitting at home with the significant, or the 6 people they only hang out with (see above). It's been a frustrating place to be when I've had to see many cool things by myself.
-People act like Madison is the only place where anything ever happens, i.e. live music, etc. I admit to buying into that when I first moved here, but the reality is that really any city that's bigger will have just as much if not more going on.
-Stop protesting. Only people around the square can hear your crowd, and they probably find you more annoying than anything.
-On that, the town (well, it seems like it) collaborates on talking like Madison's a huge city. If a Farmer's Market is the biggest thing traditionally going on in the summer, it's not a big city.
Ok, enough ranting.
Likes:
-As someone who LOVES water with fishing and things like that, Madison not only has the lakes, but many wonderful streams in the surrounding area, and with easy access. I REALLY like the lay of the land to the slight North/southwest of here.
-It really does seem to have it's own interesting culture. It's got a nice vibe to it, and is a fairly active place. The bars (mainly around the capitol) seem to have a nice variety to them, especially for being more 'pub'ish'. Very green (and not just the color of mid-July lakes).
-OK music scene for a city its size (although you could put many things there with the 'for a city its size' slogan). I saw someone post on here that if you want a concert, you have to go to Milwaukee or Chicago. In 2 1/2 years, I've seen Tom Petty, Dylan/Foo Fighters, The Roots, Flaming Lips, Black Keys (twice), John Butler Trio (twice), Bon Iver (twice), Dr. Dog, Andrew Bird, Josh Ritter, TV on the Radio, Brother Ali, The Dodos, Drive By Truckers, Jason Isbell (twice, and he's coming back), Fleet Foxes (I hope they come back

), Blitzen Trapper, and many others that I can't think of, along with many others that I didn't get a chance to see for various reasons. It seems that bands either stop here and Milwaukee both, or hit up one or the other.
While it's not GREAT all the time, the music scene does all right, although for a college town the college crowd doesn't seem to follow.
Summerfest may be the 'biggest in the world' or whatever, but that doesn't translate to the 'best'. If Toby Kieth is headlining, I put 'best' into question...

(with that being said Milwaukee does have a way better/underrated music scene; I just get sick of hearing all the rave for a 13 day drunkfest with music in the background)
-Good place to live overall, although it has its limits. Overall it's just a small midwestern town with certain things/features that make it 'Madison'.
That's all I got for now.