What do you like to do and where do you live? Are you going to need to haul stuff or not? If so how much or how big? One thing to remember if you have a truck other people whill ask you to help move stuff.
Here is my approach: What do I need? What do I want? And how much can I afford? I needed a truck for hauling stuff for working on my house or taking off the trash. It really comes in handy for towing. But I don't want a truck to drive everyday to work, or make a quick dash down to the store. What I wanted was a sports car, a convertible, to drive to work and anywhere else I would like to go. I could not afford a new car of any kind. So I compromised: I bought a used Corvette convertible that still has a lot of miles left on it (it is a 99 but people who were not familiar with the body changes of the different years thought it was new). Then I found a 93 F-250 Diesel Ext Cab for a measly $2300. I replaced a few things and I'm good to go. I have put about 5000 miles on the truck in the last year, and about 15000 on the Vette. My philosophy is that there is no one perfect vehicle. If you must have one vehicle that will do everything buy a minivan, put it on a 4X4 frame, turbo-charge it, pimp it out, and tow a trailer behind it. Oh yeah, install a stove and minifridge.