Pros: Range of difficulties; new, faster lifts; pretty good manmade snow; good grooming
Cons: Occasionally crowded; it's more of a hill than a mountain; there's not any really difficult runs;
I'm a ski patroller at devil's head, which means that I'm biased towards because I feel a lot of affection for the hill, and biased against it because after skiing 10+ hours a week there for 6 years, I'm a bit tired of it too.
That said, it's a good hill as far as midwest skiing. They work really hard to make a lot of snow (and usually do quite well), they groom very well, the terrain park ins't huge, but it's generally well-maintained, the runs make good use of the hill, and there's pretty decent variation between them.
If you're looking for steep skiing, there's Devil's Alley (from the three person lift to the skiers right), the headwall of Cyclops (right in front of the lodge), and, by far the steepest, Outer Limits (far to the skiers left, only open during the day).
If you're a beginner or early intermediate, Devil's Playground, Dante's Inferno, and The Cauldron are perfect.
And if you're intermediate, Sidewinder, Cyclops, Revenge, and Roundabout are at your level.
I can't speak much to the nightlife, but they do have a big, fun New Year's party, and there's a fair bit of live music, and several bars and restaurants, and the hotel in the lodge.
I haven't paid for a lift ticket in years, and I definitely wouldn't go a fraction as frequently as I do if I had to pay, but if you're in WI, IL, etc. and looking for somewhere to learn or not get rusty, it's a great option. If you're looking for really good skiing, go find some mountains.