I carry a Super Sherpa on the back of my Lazy Daze with a custom rack.
The Sherpa is an awesome bike for just about everything. It will run all day at 65 mph on the highway, is geared low enough for off road use and is fine 2 up as long as you don't plan on getting anywhere fast. Plenty or racks available for adding a top case, I use a small Actionpacker and a Polar Bear soft cooler to do my grocery getting and laundry.
If you can find one, they usually are in the $2000 range as they hold their value rather nicely. Kawasaki brought it back for 2009 but for some reason stopped selling it again and I've seen the 2009's selling for about 3,400 new from dealers wanting to get rid of it.
If I were looking at new bikes this size, I'd look at the 2013 Yamaha xt 250, it is now fuel injected which can be nice.