THX guys.
The bags/trailer - never ending debate around here. Unfortunately no way to demo ride both options. Probably buy both and use a combo on different trips. Those trips are starting with some short local stuff around south jersey and the jersey shore and then ranging out to the delmarva. if things go well, there's NJ to Key West. We'll see!
I'll play with the pressures to see how it affects the ride. Anyone know of an accurate bike tire gauge for Presta valves?