Sissy bar luggage - Adapt, Improvise & Overcome!
I've debated saddlebags and tombstone bags with myself ever since I brought the bike home.  For the most part with the type of riding I do I don't really need the extra storage capacity of saddlebags, and I just don't care for the way they hide the chrome.  I also tend to be just a little "tight with my wallet".  Along with a leather trunk on the luggage rack what I found was the 'frame pocket' on my medium size "Alice Pack" fits nicely over the sissy bar, rides well on the passenger seat, and provides a nice backrest on my 3 or 4 day weekenders.  It secures well with the lower straps and just one bungee around.  Plenty of accessible pockets, and somewhat waterproof!  I guess maybe I'm too cheap to buy bags for that occasional long weekend, but if I need more than rain gear, a spare t-shirt, jeans, and American Express I just don't have as much fun!  
To each his (or her) own, I guess that's why they call it freedom.