I have a 2005 GMC 2500 duramax and I tow a new 303RLS reflection (just got it) You can see the pic in my profile (excuse the salt on the truck) and it is with my winter tires 245/16's on the truck....
Bilstein 4600 HD shocks were a tremendous handling and ride improvement on my F150. I don't know if they would make much difference on the SD as it already has HD shocks, but they should make good replacements.