Wow, some great discussion already! I'll try to fill in the blanks.
Yes, the truck would be able to reach anyplace I'd want to take it.
When I pull the snowmobile trailer now, I almost always have it on my pickup as I have to take it off-site to unload. That being said, my current truck is a Silverado 1500 crew, I beleive the tow capacity is 8000# or so, and being a super short box, it can't be used for a gooseneck. I may get a new one sometime, but likely still be a 1500 as I use it for my daily driver and can't justify thousands of additional cost just to pull a super heavy trailer occasionally.
Here in NE, there is no vehicle inspection requirement per se. so that isn't a concern. This truck has a 350ci engine (I think), and would be largely pre-emission, etc, so maintenence should be pretty simple. I have a shop full of 350 engines and parts leftover from my racing days, so should be fine there.
I get the issue of larger payload on a trailer, but given the limitation of my current pickup, that wouldn't be a large disadvantage. Tree limbs and brush get dumped about a mile away, so pretty easy trip. The place where I get driveway rock is under 5 miles away, so making extra trips wouldn't be the end of the world. If I need a lot, I'm going to have them deliver in a 10yd truck anyway.
I think it would be a hoot to have a true med duty dumptruck, but as noted the expense, hassles, etc, don't allow for that.
I totally understand that the dump trailer is probably an overall better option, but is it twice as good when considering price?
I just re-read this bit; "and being a super short box, it can't be used for a gooseneck. "
Why not ?
The short box and gooseneck trailer issue is about cab to axle distance and trailer nose width.
i.e. ball to cab had better be at least 1/2 trailer nose width if you want to do 90 degree jack-knifed spin-around turns.
Unless you want some crazy wide top deck on it you can do full spins without cracking the trailer against the cab.
VERY FEW RV or horse trailers are 8 ft wide, most taper to 5 ft.
I can see a gooseneck equipment trailer being useful with a 5ft wide upper deck nose.
Not that I endorse spin turns, they are HARD on tires, hubs, just about everything else unless you are on very soft footing.