I daily a 3500. I put down almost 20,000 miles a year. I see you're in forest grove, I drive around the same area between the Couv' all the way down to Monmouth and independence. I know how horrible the roads are in Portland. All I do when I'm not hauling is run a lower air pressure. For whatever reason, I can't fathom the thought of buying a 3/4 ton and then claiming you need more truck for whatever reason. The wife and I talked it over and we decided we didn't want to the play the stupid "Trad-in" game. I want my truck to last for 20 years so I bought the biggest truck I'll ever feel comfortable driving through town and parking at home.
Also, with a 3500 series truck, they are not required to have TPMS (over 10,000 GVWR). So you don't have to keep OEM pressures even when unloaded. This means you can soften your unladen ride a bit when you don't need it.