With only one exception, I have always had vans. The one truck I did have was nice, but as Brushslinger said, cleaning the snow and ice out and off of everything is a PITA, and hauling materials when it's raining/snowing is a PITA also. Then there is security. Even a camper shell only slows down a thief.
For the vans, I have had all three major brands. I didn't like the way the Fords drove, seems sloppy. The Dodge was a good van, but they don't make them any more, and the Chevy was "mediocre" at best, the only reason I liked the Chevy was it wall tall enough to slide plywood or drywall in standing on edge, you didn't have to empty it out to get sheet goods in. The Fords and Dodges were slightly to short to stand up a 4 foot sheet, at least at the time.
Right now I am looking at the Sprinters that Chrysler is selling. The guys and girls I know that have them love them, lots of room, drive nice, and get 20 - 22 MPG average. I understand that the engine and drive train are Mercedes, so they ought to be dependable. I haven't had time to do a lot of research yet, but they are 1st on the list to replace my Isuzu NQR.
I guess it's Like Workaholic said, it's gonna depend on what the main use is going to be - to work out of, or just a support truck. Seeing as how you from the northeast, the rain/sleet/ice/snow (same as we have here in Michigan) would lean me more towards something enclosed.
I tried the trailer thing for a while, but it always seemed like if I went to do a small job, the homowner would in want something else done, but I wouldn't have the tools/materials with me, they would be in the trailer. If I did larger jobs where I could park the trailer there for days or weeks, than that's a different story, but doing jobs lasting only a couple days or so was more of a hassle.
Then fnding a place to park it while you work is another PITA in some areas. Seems like you get to the job, back it in, and an hour later some other trade need it moved for one reason or another, and now you can't find a place within 500 feet to park the truck and trailer.
I work out of a 16 foot box truck right now, but the lease is up soon, and I am going to repalce it. I love it, 95% of the time I have everything I need for a job right on the truck, a big timesaver around here where a trip to the local hardware can take 45 minutes during rush hour traffic. When I bought it 4 years ago, diesel was $1.39 to $1.49 a gallon, no big deal, now it hovering around $3.00 a gallon here and no relief in sight, and a 9 - 10 MPG, it's getting rediculous to spend $125 to fill up a truck.