I had a hitch put on by a local utility trailer manufacture for the Timber Ridge I traded in earlier this year, custom built and installed for a little under $500 with me installing the wire harness myself. I would tow a 5 by 10 utility trailer with a Polaris RZR behind it. Put me at just shy of 64 foot total length, so I was good to go in the areas I like to roam.
I will advise that you really have to plan your routes carefully as backing up is virtually impossible. I also wired a camera system as you can't see the little trailer back there at all unless you're in a fairly tight turn. As mentioned you need to do your research prior to crossing state lines, but that is recommended anyway because towing speeds and a few other things vary from state to state as well.
As for how it towed, on my setup it towed like a breeze. I've seen double setups that didn't track so well however so that's something you'll also have to consider.