A suggestion would be to consider Works Shocks (www.worksperformance.com). I had their shocks (and front springs) on my '04 V-Rod. They made an amazing difference over stock. (Tighter handling, much firmer, etc.)
To your point regarding riding 2 up, Works will match your shock springs to the type of riding you do. They're pretty good at coming up with a solution based on solo weight, percentage of time riding 2 up, etc.