Not sure I can help - but we tow a Wrangler (2 dr, sport) behind our 42 foot coach.
Flat towing is ALWAYS easier - the tires on any vehicle will be more reliable than nearly EVERY trailer tire....and you wont have to worry about where you can store the trailer (mosts parks dont have the space)....backing and deal w/ a trailer will be nothing but a PIA...especially if your towing doubles.
In <impossible> situations (where I couldn't back up w/ the toad) I have disconnected and put the wife in the toad in less than a minute (all I have to do is pull 2 pins, 2 chain hooks and the electrical connection & im disconnected / reconnected).
Youll need to check (each) states laws for towing doubles and length....over 65 feet will make you illegal or (require permit) in many states.
State Maximum RV Length Restrictions along with other (height, weight, etc) can be found at the RVIA site
CLICK HERE
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Don R.
'04 Haulmark (M42386) 42', 2 slide, 10kw -
Pictures
'04 F350 CrewCab Longbed 4x4, 50g aux tank & gear vendors dbl over