I'm 275, "The Ball & Chain" is around a buck and a quarter. 2-up >95% of the time.
70% of the time, the Chopped TourPak and bags are loaded for our "Sport Touring" excursions.
She gets 1 bag, I get the other and the TourPak is community property. We have the TourPak packed so that we can stuff our jackets in it, if it is too hot to wear them.
'Got her carrying the tools in her bag, since her clothes are 1/5 the size of mine 'he 'he
When I was shopping suspension, I spoke with Progressive and they told me that a lot of people get their heavy duty stuff and are dissatisfied with it.
Here's what is in the '09 SERG
http://www.harley-davidson.com/store/premium-double-cartridge-fork-kithttp://www.harley-davidson.com/store/hand-adjustable-rear-shocks (12" std. on '09 SERG)
'Did the shocks first, then the forks a little while (3k) later, it seemed like it took the forks around 500 miles or so to "settle in" and I adjusted the shocks a little firmer ( a rotation or two ) 2 times, hit the sweet spot and the bike rides fine solo / empty too...
I believe my Tech said that he used a little heavier fork oil when installing the fork cartridges, I think 15 wt instead of 10wt oil. He also mentioned that the fork oil should be changed at 50k on the forks.
'Been fortunate to own / ride some tricked out bikes (street and dirt) over the years, I am impressed with this set-up. A smooth supple ride, not overly firm, the tires always feel like they're in contact with the road, brake dive is next to nil, not bouncy, no shudder, hold an easy line on those high speed Western Sweepers or the tight twisties, and when they do bottom out (not very often) it's a cushioned thud, not driving your tailbone through your neck...
To me, very well mannered all the way around

PS:
I did have the GlidePro Bushings installed in the '09 (mostly because I got free labor) while the drivetrain was being Built this past winter, (already had around 15k on the F&R suspension upgrades) the bike was down for 6 months, so it's hardly fair to say how much impact the GlidePros have on the handling of the new frame (the GPs along with the Commander IIs turned the '05 SEEG handling into a sport bike!) On the '09 the GPs and probably, the S&S .0005 (installed w/Timkin) Crank really smoothed out the vibration in the seat, bars, & footboards. I would do the GPs again...
Dan, you might try upgrading the forks first with your 440s and play with the adjustments on the 440s, and see if y'all can find a sweet spot, if not the shocks are easy to change out...