I've been to JHMR in each of the past three years, and there's really not a lot to complain about. The terrain is very diverse and it's pretty easy to get from one side to the other, especially with the new Marmot chair they added last winter. The one thing I will say is that if you ride regular and you aren't comfortable riding switch, the mountain naturally funnels from right to left, so the 10 minute heel-side traverses can really burn the legs!
The START bus runs about every 15 minutes to Teton Village. It's $3 each way, and many of the hotels sell tickets so you don't have to worry about having $1 bills on you, so stop into one near your timeshare and ask. Within town, the shuttle is free. As for food and nightlife, the Silver Dollar Bar at the Wort hotel and Sidewinders (sports bar) are solid choices. Mangy is great for après, but it fills up really quickly.
There are a ton of options for great terrain; too many to list. But if the headwall is open, the hike up Pepi's Bench is worth it. If you get a powder day, the lines for the Tram and Gondy will be huge, so hit Après Vous to warm up the legs for a few runs and wait for the lines to subside. There will be plenty of first tracks left for you when you get to them...