Diesel Bombers - Newbie in Tampa FL area

Hey guys

I'm a total diesel newbie.

So new I haven't even bought a diesel yet.
I'm actually in the process of trying to figure out what I actually want to get.
Which is what brings me to this site. While surfing around, I've seen a few forums, they all have decent info, but this one just seemed a lot better than a lot of the other ones I had surfed through.

I currently drive a 2003 F150 Lariat SuperCrew.

I bought the truck with cash after a settlement I got from getting hit by a drunk driver*.
At the time, I was torn between the F150 and the F250. I really wanted the F250, but I didn't know much about diesel and basically talked myself out of needing that much truck.
So I got the F150. I like the truck. I use the truck, but I've never really fallen in love with the truck.
It is kind of like when you were in high school, and you could choose between the really hot girl in class, and the average girl. You didn't know if the hot girl even knew your name, but that average girl was all kinds of into you. So you start dating the average girl and things are ok, but you still long for that hot girl.
Yeah, its kinda like that. lol

I own my own landscaping company. We do everything from simple lawn maintenance, to custom landscaping installs, to custom patios, full custom outdoor kitchens to full on back yard make over type projects.
I also go to college** across town. (I live in St. Pete, and take classes in Tampa) So I'm in my truck a lot.
So at this point, I decided that I'm going to dive back into the research and figure out if the F250 really is the best fit for me and all of that, and get my truck cleaned up and sold before I put too many more miles on it. I'm about to turn 130K as it is, too many more miles and I'm not gonna be able to get the thing sold for a reasonable amount.

Currently, my truck is my daily driver. I'm saving my pennies for a sport bike in the near future. A 2006/7 Kawasaki ZX10-R. Then I'll be riding as often as possible. But the truck will still see a lot of miles as I'll be using it for my business. Half of the time, I don't have a trailer, but I do have tools and supplies in the back. When I do tow a trailer, it is either my enclosed 14 ft trailer, with full equipment, or an open 12 ft trailer, full of equipment.
Other than that, I rarely tow heavy stuff. Maybe every few months do I get a big load, like a trailer full of pavers/tile/ etc, or my sister's broke down car.
From what I've gathered, all of the trucks this size can handle the kinds of loads that I'll be dealing with.
MPG is a major concern.
I'm really drawn to the looks of the F250. I'm a fan of the 2000-04 body. I really like the 2005-07 body style.
But, being so new to the world of diesel, I'm not committed to what truck I want to buy, so any advice, input, tips, tricks, cheat codes, etc, are hugely welcome.

* It was the middle of the night, a few years ago. The cops estimated his speed at over 100mph. I was going 30/35. I saw him coming up behind me, I could tell he was speeding, and before I could change lanes to get out of his way, he rear ended me. I was in a 2003 Toyota Celica (girlfriends car) He was in a brand new Toyota Camry. He hit me so hard that my car rolled over two complete times. The end result was a surgery on both knees, surgery on my right shoulder, and 6 herniated disks, two in my neck, one between my shoulder blades and three in my lower back. Sucks having back problems at 24 years old.

** I haven't declared a major yet. I originally wanted to get an engineering degree, but I'm really drawn to the business world. As it stands now, I think I'm going to get a degree in Business, and then pursue the engineering should the cards fall that way.