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.
john