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?