Al, I don't think the HD shocks are going to sag much with 220 lbs (you and bags) just sitting. Surely not 3/4 of an inch... maybe a mm, but not much.
I'm not sure the std rate springs are going to settle with rider and bags much either.
I believe you would like the ride of std rate better for all solo riding, and remember every half inch you go lower with the shock, the stiffer the springs will be (with less total travel), whether std or HD springs are used. If I had a passenger a couple times a year, I'd set it up for me, and do the best I could for the passenger rides.
I am thinking you might be better served with air shocks. They will not have the full performance of the 440s (esp with rebound), but they will give you more flexibility. PS 416 But I don't know much about them. Call Progressive and ask about them. Only lifetime warranty is the 440s.
It also sounds like you could use some built up sole boots, with great traction.
Like these:
http://www.lapolicegear.com/ro6mealbow.html http://www.lapolicegear.com/rocky-alpha-force-boot.html