I have the full set of the insert bags and also the frunk suitcase on rollers.
I do not ride with the insert bags in the cases. For whatever reason, I just do not like them. I did use them on our 2010 trip to Whitehorse and Skagway.
I dont carry anything in the side saddle bags. If it looks like, or rain is forcasted, I am wearing the Firstgear textiles, or my revit pants with the rain liner--which takes care of the rain.
My back trunk carries my fold up walking stick, a cap, extra gloves in various sizes, and a couple bungee cords.
The frunk carries the manual, the stock tool kit, a set of torx, some locktite, an extra pair of pliers, insurance papers, akspyderladys purse, and whatever else we need for the days ride.
Only one helmet will fit in the frunk. We use Nolans. We usually leave the helmets on the seat, but the bike is in full view of where we are. I have had people come over and look, but never tourch--so I don't worry to much about theft.