The Highlands is like the peanut butter of a pbj. Aspen and snowmass are the bread, buttermilk is the jelly, but highlands is what you really came for. It's the meat of the sandwich. Overall, the place is tiny compared to Snowmass, and, strictly speaking, if you aren't here to hike the bowl, then I would by far suggest that you opt for snowmass. However, that bowl is such an amazing slice of heaven. The hike is brutal, even by Colorado standards. Mainly this is due to the hikes length, which is much longer than say getting off the imperial lift at Breck and hiking that extra 300 feet. No, this is a much longer hike, and all above 10,000 feet. Be prepared to take a break and move over for the rest of the crowd taking the same hike. But still, the bowl is something that every skier has to do before they die.
Of course, Aspen is a great town, even if it is horribly expensive. The hill looks quite family friendly, but if you have kids, I would shuttle them down to Buttermilk for some easier terrain.