I installed a Roadmaster on my '01 F350 DRW and it is WAY better than the thin stock anti sway bar. Best bang for the buck when compared to shocks, airbags, and stable loads that were also all installed.
I too had to make that decision when buying mine 5 years ago. Since I haul a boat on 95% of my trips I liked the 990 better since it allowed a shorter hitch extension. Plus, when on the inside it felt to me that the added length didn't make the camper feel much bigger. What do you gain, a coat closet or something like that (remember I am comparing 2007 models). That minimal closet/cabinet space was not enough to override my engineering mind looking at the shorter hitch extension.
4000lbs in the bed? I have yet to weigh mine but don't most of the posts on here say they are closer to 5k when loaded up and ready to dry camp with water and everything?
What year 3500 you looking at? If you are worried about following the payload rating exactly and never going over it the Chevy had the lowest GVWR for the 2000 era trucks I was looking at. Newer trucks have increased. Heck, my 01 dually F350 GVWR is 11,000 while my father in laws 2011 SRW F350 is 11,000ish lbs.
Good luck with whatever you buy. John
I started with a srw with my 990 and after one eason my wife would not ride in it and took the kids in a seperate vehicle to get to the campgrounds. So now we have a drw and love it. Like campn4walleye says, it depends on your comfort level.
As for driving the drw in town, I have no issues taking it to the store or running down the main drag. The only thing that makes me nervous is when road construction puts out cones and funnels traffic down. That gets tight. For everything else you learn the limits of the truck and know to park farther out, not do drive thrus, etc.
I also put about $1k into upgrades for the drw. Rancho 9000s, stable loads, airbags, Roadmaster anti sway bar. The roadmaster was the best bang for the buck of all the upgrades.
What part of Oregon you in? I am near the north eastern corner just across the Columbia. If you are close enough you could come see my 07 990 in person and take any pics you want to get your info.