What
@riverc0il said.
I made multiday visits to JH in 2015, 2018, and 2020 (ten days before the pandemic shut the ski world down). It's a fabulous mtn, but it was busier and busier for each of those visits. It is a premier example of how joining IKON can significantly increase the popularity/visitation of a ski area. Having said that, if you've never been there it's a "must ski", just bring some patience.
Rendezvous Bowl, 2020, you have to ride the tram to get this view, a strong intermediate can do this terrain and you won't want to miss it:
The crowding is mainly an issue with the tram, the Bridger gondola, and the parking situation. If you see a small line for the tram - do it, because most of the time it's long. Probably best bet for the tram on non-powder days is early and late, but occasionally there are lunch time lulls. The Bridger gondola can get backed up in the mornings, but is mostly fine otherwise. The newer/shorter Sweetwater gondola is not nearly as busy and trail traffic on that whole side (lookers right) of the mtn is generally lower than the rest of the layout. That side, including the Apres Vous chair, is a good place to escape most crowds even on powder days.
Loading the tram, 2020:
The upper mtn Sublette and Thunder chairs have some world class skiing when you don't want to mess with the tram.
This is a friend in one of the Alta chutes off the Sublette chair:
Staying at a friend's house should be a really fun way to go. Not sure if you'll be on a bus line for that, otherwise you'll probably have to drive to the free community lots about halfway between the town and the ski area and catch a free bus from there. Or you might be able to drive all the way to the ski area and park there. Your local friend will know what's best.
My non-skiing wife was with us on my 2020 visit and we did some alternate activities and enjoyed visiting the nearby National Museum of Wildlife Art for a couple of hours. The town is worth a stroll on an off day. There is a wildlife refuge near town too, that can be a diversion to see buffalo and sheep.
Chief the Buffalo by Robert Bateman
I'm sure your local friend will have restaurant recommendations too, but FYI I enjoyed a couple of meals at reasonably priced Bubba's BBQ on the edge of town in the direction you are staying. We had a nice, pricier dinner at the steakhouse in the basement of the famous Million Dollar Cowboy Bar in downtown Jackson. In 2020 we stayed in Motel 6 for crazy good rate of around $78 per night. The room was small, but pretty decent.
On my 2020 visit to the area I drove over and skied Grand Targhee for one day. It was a breath of fresh air compared to hectic Jackson Hole. The skiing is not as challenging, but still plenty good and the scenery is off the charts.
I stayed slopeside when I got a good deal at Snow King Resort in 2018, but did not ski it because I had time for only two days at Jackson Hole and had to leave the area for a long drive to Revelstoke. It's smaller than JH or GT, but looked like you'd have the whole place to yourself at that time.
Bonus JH shots:
The Hobacks behind these friends is a large "side country" area that is fun to explore, but conditions can be variable. Ask around before entering it.
My son entering Corbets Couloir in 2018:
