Some background on my experience:
I live in upstate NY and have extensive off-road and deep snow/blizzard driving experience, as well as towing and plowing. I have also lived in NYC, and Boston, so I have driven all of the northeast highways under all different weather conditions. I think I know your (our) part of the country pretty well. I have owned all of the following for at least several years each:
1980 Chev k20 with hd springs (k=4wd, 20=3/4ton) It was spec'd originally as a powerline maintenance truck for a local power company - a real battleship until the body (not the frame) rusted off.
1987 Nissan Pathfinder - garden variety SUV with all the trimmings.
1990 Chevy K1500 short bed (6 1/2 foot bed, 4wd 1/2 ton)
1996 Chevy Tahoe - a 1/2 pickup truck in SUV clothing!
1997 Chevy K2500 extended cab short bed with HD springs and towing package
Here's my advice, after reading all of the post straight through:
Diesel engines are hard to find fuel for if you don't know exactly where to go. As you travel out of your home territory, you may have to hunt for a station with diesel. Used to be every gas station had a diesel pump, but now, I have to go out of my way to get diesel for the 2710. Probably be even harder as you venture south toward the city. They also have poor acceleration characteristics RELATIVE to a gas engine. Sometimes we need to speed up quickly to get out of harms way.
The mid-size truck class (both domestic and import) are not built to take the abuse of hauling and working day in and day out. If you want a truck to commute in, fine, but if you want to tow and use it as a 3rd vehicle for working, get a full size.
In the full size class, the Toy(ota)s are too new and too few. If you need a new water pump for your v8, how much do you think it would cost to replace the Tundra part vs a chevy 350 part? How about a used radiator? Even though they improve the engines each year, they are still based on the same basic engine design. This is true of all domestic brands, but the venerable chevy 350 is hard to beat for parts availability.
If you really start using the truck for projects, you will probably find that hauling gravel and topsoil from the local gravel pit is what you do most that taxes the truck. You can easily overload the weight ratings with a 2/3 full bed full of topsoil (<2yds). If you find yourself if this position, HD rear springs are a good bet. You can get these by finding a truck that had the towing option. Also, the truck brakes are bigger on the 3/4 ton trucks, as well as on trucks with towing packages.
Automatic transmission. The hunting issue on hills can be a concern, but there is a tradeoff - it is really nervewracking to try to start from a standstill at the top of a steep hill - especially when that little nissan sentra is 3 feet behind you! You can still manually shift the autos on a long steep incline, and this will eliminate much of the hunting.
Garage clearance - My truck sits up high and still fits (just) into my 7 foot garage door. thew Dodges look like they might not.
My conlcusion - Get a 5-7 year old 3/4 ton (25xx series) 4WD extended cab short bed pickup with towing package. You can probably find one for about $10-15k that you wouldn't be embarrased to be seen in. As for brand - You might have noticed I am a Chevy fan. Fords are probably just fine, but I don't like the interiors - too spartan in my opinion. The Dodge engines were a little dicey back then. they had just introduced the newly designed RAMs, and they had reliability issues for a few years. Check the consumer reports reliability stats for the specific year and make you are considering. Some of the known problems may have been paid for by the previous owner, but be careful.
Finally, you will find yourself off the road if you get one of these things. Some of the back woods around me probably do look a bit like Afganistan. It can be for fun, or it can be for work, or it can be because you made a bad decision and ended up in a ditch and decided to keep moving so you wouldn't get stuck, but you will end up off the road. Lets just hope its not on one of your infrequent towing trips.
Just my opinion.
PaulT