Curt,
I don't know Mustangs, but Doug is right on with his take on it!
I think the real key here is just how well you know your vehicle no matter what it is and what you can do to it on the road if you need a repair.
As you know, I do a bit of traveling with my old car.
I know it well, and am able to make repairs if ever needed, though I have never yet had to make a roadside repair...because I know it so well.
(Well, I have had a couple flat tires, and had to wire up a cracked manifold once...)
I use it often enough that the slightest change in anything is instantly apparent...and corrected.
In the old car world, there are drivers, and there are show cars.
Each are nice in their own right, but it can be comical to watch the owners of the "perfect" looking show cars struggling to get them running, or listening to them cough and sputter as they attempt to get them from their trailers out onto the show field.
(Many can't get around the block under their own power).
Many of these owners obviously spend every free moment waxing and polishing instead of taking the time to understand and maintain the drivetrain...
A pile of plastic trophies is heaven for some, but being able to hit the open road anytime for any reason, for any distance without a care is why I'm in it.
If a vintage car owner doesn't have 100% faith in the car and their ability to deal with what may, then it probably isn't a good candidate for towing a trailer...
In general, if an old car can be driven for a hundred miles straight without any issues, it can make a thousand.
Rob
<img src="http://img.photobucket.com/albums/v284/1948rob/hill%20climb%20campout/ontheroad2-1.jpg?t=1180874954">
Waiting for "someday" will leave you on your deathbed wondering why you didn't just rearrange your priorities and enjoy the time you had, instead of waiting for a "better" time to come along...