Cruisers, like the Harleys you are looking at are fine for local and around town riding, but for me the feet forward and bar position makes me feel like Rocky the flying squirrel on the highway. On longer trips of 100 miles or more that gets really tiring. Also the Softail designs have limited rear wheel travel and can be pretty brutal on anything less than smooth pavement. The shock seems to go straight up your spine. Since your feet are out in front of you, it's not very easy to lift your butt up over larger bumps.
The most comfortable bikes are probably the Sport touring (Honda ST1100/1300, Yamaha FJR, Kawasaki Concours, and several BMW RT models) and the Adventure Touring models (BMW GS, KTM Super Adventure, Yamaha Super Tenere, Suzuki V-Stroms, Triumph Tigers, etc.)
The Adventure bikes tend to have much more spacious riding positions and the longer travel suspension gives them a superior ride. A down side is they tend to have higher saddle heights which can be an issue for the inseam challenged.
I have both a Honda ST1300 and a Yamaha Super Tenere. Both are super comfortable for local and more importantly, long distance travel. I slightly prefer the Super Terene for it's greater leg room, but the Honda ST has better wind protection and with its lower seat height is easier to mount/dismount.