While I'd agree that the DRW trucks are the best looking and have lots of advantages, if you live in the city or have to drive into the city a lot, do a lot of on-street parking, that kind of thing, be realistic about how often it will be a PITA. I think the biggest thing to think about is where will you park it at home and at work, and anywhere else you have to go every day. If all are easy, then I'd say go for it.
I'd love a dually if I lived in the country, but living in the city, just having a LWB truck is a major PITA. Obviously it can be done - there's plenty of big DRW commercial traffic all over the city, but I couldn't park a DRW truck in the garage at work, and the rear fender would for sure get clipped sticking out into the narrow streets around where I live and often have to park.