Being a gym/fitness rat, I'm in good shape. However, I'm not used to the elevation. I'll try to make this hike after acclimating a bit.
True acclimatization to a higher altitude only happens after a few months. The best thing you can do to prepare yourself is interval training or cardio that builds up your wind and lowers your resting heart rate.
Lots of swimming or long distance running.
We are renting a car as well. Sounds like it might just be easier to drive up in the morning rather than stand on the shuttle for 30 mins at a time. I get enough of that bullshit riding the train everyday to work.
You will probably still end up taking the START Bus in. Jackson is a ski where you really do not really need a car. The (extremely) rich folks who run things in Jackson do what they can to discourage skiers from driving in everyday to ride the mountain. There is a pay-to-park lot close to the base of the mountain, but there is a free-to-park satellite lot just a few miles down the road.
All of the START Buses on their way into the village and on their way back into town stop there. If you already have a car, I would drive to the lot, park there and just deal with the 7 minute, free bus ride to the resort.
I feel like since I'm there I need to hit Taghee up at least once.
Bring a book or magazine for the ride home. Don't forget to take a picture of the 3rd largest potato in the world in Driggs :-)
Thanks for the tips man