[Towing with a Jeep Gladiator]

We are looking to buy an Oliver.  The tow vehicle will be a Jeep Gladiator which has a GVWR of 7650 pounds.  While I'm sure it can tow the 18-ft Oliver, does anyone know whether it will tow the larger, 23-ft trailer?

[Northern winter camping]

We're looking into the Oliver.  One of the things we'd like to use it for is winter camping in the ski areas around us.  We're in Northern New England so it frequently gets down below zero at night.  How comfortable would we be in an Oliver?