I never came back to this thread to say what we actually did do, because this was the Cloudveil-specific thread and we didn't stay there, but I'm pretty sure I posted "somewhere".

We did do the mini-road trip thing, and I'd do that again - while we also usually like to unpack once, I'll never regret waking up to the Tetons right outside my deck. We stayed at Signal Mountain Lodge when we weren't in Jackson. And we stayed at the Homewood Suites in Jackson which was just a block or two north of town in a leafy residential area. I used Hilton points because, as you all know, cash prices are outrageous. I'd stay there again. Cloudveil was just ridiculous with all their fees, even though it looks very nice. We had a "suite" at the HWS for a fraction of the cost.

As far as Jackson goes, it's very touristy, and since we fall into the "in bed by 9pm camp" ourselves, it was fine. I didn't notice any affluent folks, ornery or otherwise, just regular folks like us. We didn't eat at the Snake River or any of the other "top" places, but had a nice dinner at an Italian place a block over from our hotel, and a disappointing one at "club something" a block south of our hotel. And good pizza in a place that was an old theater. Didn't look up the names.

We loved the wildlife art museum just north of town, and also took a walking tour of Jackson with a guide from the historical society.

What was interesting was that we decided to shorten our trip and blow off Yellowstone and do it another time....we left the area the VERY DAY before the devastating rains came last June. We would have been stuck or worse.

Thanks for jogging my memory about planning that trip to Yellowstone! And I would definitely dip down to another night at Signal Mountain (and not Jenny Lake Lodge where we had lunch, nor Jackson Lake Lodge, but dear old worn around the edges Signal Mountain Lodge).