Lodging at Aspen can be expensive. But there are deals to be found as well. Check the Wildwood lodge, where ESA is being held, as well as the Poklodoki (sp?). You might also be able to score a reasonable condo through VRBO. Skier visits were down last year, and the economy has not recovered, so there probably are deals you can score if you look hard enough.
Snow is, well, weather related. So conditions can be variable whereever you go. For all the advice you've received about heading to Steamboat, I can assure you that I skied Steamboat in years when there was not much cover. You take your chances, or you wait to make these decisions until you know what the conditions are, and likely pay more. The two times I've been to BS the conditions have been tremendous. Last April at ESA was the best skiing of my life -- 3 days of waist deep powder. And I was given the nickname "snowblower" for a reason.
I doubt that the snow conditions at Big Sky differ that much from Jackson, but Tony will probably weigh in with empirical data analysis on that score. They are more or less in the same weather patterns, although BS is about 100 miles north. There is no doubt that BS does have areas where rocks lurk, which leads to the rule the locals apply: if there are no tracks, don't venture there.
I've looked back through the thread and cannot see where you stated when you were thinking of going. If it is early season (before Christmas), I'd say that you are likely to have major closures in terrain wherever you go. Even Steamboat has had tough early conditions the past couple of seasons. The snowpack generally doesn't accumulate to realiably offer good off-piste skiing in CO, WY, and MT unitl the new year. So, if you want a deal on hotels and airfare from booking now, then pick a place and realize that you may have less terrain than you would really like. That's kinda part of skiing. I certainly had less snow than I would've desired and it was much warmer than optimal when I did Steep and Deep camp at JH in 2005. Did it ruin my skiing? No -- it's all skiing.