Do you enjoy paying $300 every time you need to service the truck?
Do you think stopping at just one station in search of fuel is stupid? Do you like having to remember where the station that sells diesel is located and then calculating how far you can travel away from it before risking running out of fuel?
Do you constantly feel the urge to leave Prius drivers in a cloud of your exhaust?
If these describe you - Go Diesel !!
Otherwise, if you have went this long without needing one...you probably will be fine now.
Used diesel in my experience is just asking to overpay and probably take on someone elses headache. Theres a reason diesel owners keep them forever. Trade in is not favorable and dealers know used diesel trucks are costly to recondition.
Diesel has its practical applications...but for light duty 1/2 ton trucks - go gas. If towing is a daily need - move up to a 3/4 ton gas first. If its not big enough - much easier to trade out of than a diesel resale wise.