Geo Biker, I live in Tuscumbia about 2 miles from Shoals Outdoor Sports, they gave me a thousand more for my harley than any harley shop in a 150 mile radius, and they gave me a great deal on a new 2013 Cross Country Tour about a year and a half ago. They will put you on one for a test ride, and like someone said, plan on trading because you will! Bring your title or your loan info. Heck, call me and I will go with you to make sure they don't feed you a line of bull, ( which they won't).
You will definetly want the tour for the traveling your talking about, then around town, just take the trunk off, it only takes 5 minutes.
Being from T-Town, I'm going to assume that you are a Bama fan, you need to see my bike, I had a guy do hydrographic dipping on my dash and trunk speaker pods in the Houndstooth design, its not that way in my sig but I put pics on the show off page, look for them, or better yet, get in touch with me for a personal look.
As far as being comfortable, I just got back from a 3 day, 1400 mile ride, and felt comfortable the whole time. PM me, I don't mind helping you and showing you all I know about these bikes.
P.S., I was just at the dealer last week before my trip and they had a two tone blue and silver CCT with 4 miles for $17,799, ad tag said $316-$326/month payment,suggested retail was $23,099, savings of $5,300