I'm not quite sure what your concerns are over miles, the Rocket is alot more comfortable than the Tiger. I commute from Delaware to Philadelphia nearly everyday at 80 miles round trip and enjoy the hell out of it. The wife and I put over 1,000 miles on it going to Niagara Falls this summer with lots of luggage. We weighed in at 1300lbs gross.
As far as luggage, I have a set of K-Drive saddle bags and a large leather sissy bar bag that I leave on the bike most of the time. I should have gotten the BIGGER K-Drive bags but these work just fine. I recomend the K-Drives if you plan to take your saddle bags off alot, the brackets that stay on the bike are chrome and nice looking when the bags are absent. But I think a paint matched set of hard Beetle Bags would look awsome on the Roadster, especially the flat black version. The Roadster exhaust would really compliment the Beetle Bags.