I ride something similar to that bike, an Electra Rat Fink. While the riding position is quite comfortable, you might have a problem climbing very steep hills, due to the low seat and feet forward position. My bike has the same Nexus rear hub, and shifting is very smooth.

As for comfort, I never go more than 10-15 miles while riding mine. Personally, I don't think I would have a problem going farther than that.