Mad, you need to give a little more info.
- Where are you starting and where are you going? How are you getting to the trail? Do you need a shuttle?
- 2-5 nights is a big difference in the amount of food you should bring.
- Your 40 degree bag will be fine.
- Tarping out is fine for some, not for others. If you have not tarped out before I would recommend you bring your tent.
- I agree with part of Trekking’s recommendation. However, Roan Mountain to Damascus is 88 miles, difficult for 5 days if you are just starting off.
I suggest starting at Carver’s Gap (by Roan Mt.) and hike north over to Watauga Lake a total of 59 miles. This is a beautiful section, truly one of the best in the south. In this section hike you would see the Overnight Shelter Barn, Little Hump and Big Hump mountains, the Apple House Shelter, cross US 19E (do not park here), Kincora Hostel, Laura Fork Falls and Lake Watauga. There are several shuttles in the area. I suggest parking at Kincora (contact Bob Peoples) and let Bob shuttle you over to Carver’s Gap. You can then walk north back toward’s Kincora (one of best hostels on the trail). Lake Watauga is a one day hike from Kincora, Bob could pick you up and take you back to your car.
Another suggestion is to hike from Lake Watauga to Damascus, a 40 mile trek. This may be more in line in what you can hike. The last 20 miles is all down hill.
Just thinking about that section and I may want to join you. However, I can’t get off work until the end of June. Good Luck with whatever you do.
bilko