My truck is not a daily driver, but these are my observations:
I find my overall length to be more of an issue than width, but width does play into it - Tight parking lots or garages are difficult when you are 22' long because you need to pull in more square into spots when you are 8' wide. As long as I can find a parallel spot long enough, I have no issues parallel parking and will always collapse my street-side mirror.
Short commutes are better with a gasser, but I would not have a problem using a diesel if my commute was for a length of time at highway speeds where everything can get up to temperature. Since you do not have the typical elevation changes we have on the west coast, the gasser will not see thin air that often and will be more comfortable towing more weight than in my area with 3000' variation just outside my doorstep.
A DRW will hydroplane more in wet weather, so watch your speed in heavy rains when empty. The flotation of the DRW will actually help you if you get in soft sand, but a limited slip differential would be helpful in any 2wd pickup. Mud or wet grass will require something under the wheels (old carpet scraps work well).