I've been going through something similar in trying to decide what to buy. I currently have a 98 F250 4x4 regular cab, long bed. It's been a great truck and since it's paid for, I've held on to it a bit longer then I really wanted to. I'm a contractor and I haul tools and supplies to jobs all over the place. I've found that the 8ft bed is either too small, or too exposed.
What I really want is a place to keep all my tool boxes so I don't have to fear they will be stolen, or out in the elements. They also take up a huge amount of room in my bed when going to some jobs, and that's created issues with room to haul materials.
I also don't care for how stiff my ride is. I'm sure it's the 4x4 aspect of it, and maybe that it's a 3/4 ton.
For me, the crew cab solves my tool box issue. I can load up the back seats and have everything that I need with me in a secure location. That leaves the bed open for hauling stuff. With the tailgate down, I think I can haul most anything that I could haul with my 8 ft bed.
I'm currently looking at the newer F-150 crew cab, two wheel drive, short bed trucks. Nicer ride, more enclosed storage and enough room on the bed for most jobs.
I have a 16ft trailer that I use when I need it, and I get matterials delivered on bigger jobs, so for those times that I need more then the short bed will hold, I have plan B.
Since I'm not hauling heavy loads, I'm looking for the smallest gas V8 that I can get. I've thought about a V6, but they don't seem to be very common and Chevy is the only one that I've actualy seen with a V6. I like Ford, so that's pretty much what I'm limiting myself to buying, and that means the 4.6 V8 engine that is suppossed to get 15 city and 20 highway mpg. I get 14 right now with my F250 4x4, 4.6 V8, so those numbers are probably pretty close to being accurate.
I've found that my local dealers have trucks listed on Ebay for less then on their websites. I've aslo fond that for some reason, I can search out in Dallas, which is 100 miles away, and find a very similar truck in miles and features for about $2,000 less then my local dealers. I haven't gone in to negotiate, but for that much money, I'll give them the oportunity to match that price, or drive the two hours.
Good luck on what you decide to buy. I'm still on the fence, but think it's something that I need to do fairly soon.
Eddie