[A/S] truck advice - new vs. classic, do i or don't i (lots of q's)

["Brian Wittling" <kdfman@xxxxxxxxxxx>]

Hello again,

Thanks to some wonderfull grandfatherly advice by the owner of a FS 
trailer I visited, I think I've decided that my '58 Plymouth Fury 
wouldn't exactly be the best choise to pull an Airstream, even once 
in a while. It's got the muscle - 300hp, 290ft-lbs torque, heavy duty 
brakes and suspension, BUT being one of the first muscle cars, it was 
made for the track, not the tractor-pull! The 3-spd cast iron Torque-
Flite does not, and cannot have an oil cooler added, and the car sits 
really low to the ground - even with the new rear springs that put 
it's arse up in the air like a feline in heat. All the class IV (and 
you DO need class IV right?) hitches I've seen would certainly drag 
the ground for sure. This might entertain the kids in passing cars 
with the sparks, but not too great for me eh. Plus, it only gets 
(an "economical" according to the sales literature) 8mpg with just me 
in it, and as the man says, if I'm going to be homesteading I may 
just want to haul stuff like um, water and fuel and things from time 
to time eh.  Plus I'll have the added task of moving 3 motorcycles 
(one a sidehack rig), 2 scooters, 4 cars, a truckload of parts, and 
personal belongings with me to New Mexico. Not to mention the 
Airstream itself, from whatever corner of the Earth I end up getting 
one from.

So, with wounded heart, I must consider an actual TRUCK I suppose.
I'm needing some tips in what to look for, new vs. classic (50's-
60's) and what will do the job.

Pros/cons:
New: Must be Dodge, must be deisel (if i gotta have a truck, may as 
well run it for free on WVO), 3/4 ton (hate duallies), factory tow 
pkg., manual trans. is H-D cooling and tranny cooler really needed?  
is 4.11:1 rear really needed with the Diesel?
Pros: less maintenance, less repairs, warranty, diesel option, low 
operating costs due to running on WVO. air conditioning.
Cons: expensive repairs - can't work on it myself, expensive to buy, 
have to give up my beloved VW TDI. higher insurance. looks doofy 
pulling a vintage Airstream

Classic: prefferably Dodge, well maintained and in good working 
order. Body must be acceptable, but not perfect. V8 a must, manual 
trans.
Pros: I can work on it myself, low repair costs, low insurance, looks 
good puling a vinatage trailer. fits my personality. low purchase 
costs, can keep my TDI.
Cons: possibly less reliable, more frequent maintenance, no diesel 
option, no A/C most likely, hard to find in good shape. higher 
operating cost (gasoline, MPG). 

Also I've never been a "truck guy" so I'm not familiar with classic 
trucks... what models, styles will do the job described above?

Whew!  OK, I think that's it for now...

Thanks everyone!

Brian "the young one" in StL