Sounds like a fun adventure.
I tow a box trailer that has its own brakes (a must) and loaded it's about 1100#s, which you'll want to figure out how much you can safely tow with your Jeep. With your Jeep, I think you'd want to go lighter? A popup would probably be heavier then a basic box trailer with an RTT on it.
My trailer has a Tepui RTT
on top that folds up in minutes (tucks away under the cover very well). I specifically have their Ayer, which I believe is the smallest RTT on the market at 95 lbs. as I'm always trying to limit weight when towing with a Jeep. You can see my trailer link in my signature. Any questions, let me know or see my thread.
P.S. Also see this trailer forum as you'll see trailers that are custom built and light for small vehicles to tow. http://tventuring.com/trailerforum/index.php