Chicago to Gatlinburg Ride -- advice/suggestions requested

[emptysea]

Hi, fellow CB1100ers!

I am in charge of planning 2014's annual "big trip" for my little group of biking friends here in Chicago. It's snowy and cold here today, so I cannot think of a better way to spend the afternoon than planning for this trip, but I could use a little help.

Here's the high-level view of the trip:

Dates: probably the first week of June, 2014
Loose plan: Ride from Chicago to someplace close to Cincinnati on Day 1. Ride to Gatlinburg, TN on Day 2. We'd rent a cabin or house for 4 days or so near G'burg and use it as a base camp for rides in the area. I know we are going to ride Tail of the Dragon and we (or at least I) will take a day trip to Chattanooga to visit my best friend who has been very ill for a very long time.

Here's some things with which I could use some help:
1. Places to stay near Cinncy...are there any cool little towns near there with a hotel or B&B walking distance to a decent (preferably local) eatery?
2. Anyone have a contact for decent vacation rentals in or near Gatlinburg?
3. Any route advice for the trip from Cinncy to G'burg? I was thinking of stopping at Cumberland Falls, but otherwise I'm looking for points of interest and fun routes.
4. Any advice for 1st time riders at Deal's Gap? We've got 3 Wings, a CB, and a CTX in our group if that helps.
5. Any ideas on things to do besides ride? Rafting? hiking? Etc.
6. Any other "not to be missed" roads to hit while we are in the area?

Any help on any of this will be GREATLY appreciated!!
Thanks!!
Matt.