EDIT: I just saw that the OP has solved his issue but I will leave this up here for anyone else who needs the info. Any other questions about towing or trailers just PM me or email me at Logan@AllProWest.com
Like I said, I do this everyday with customers and a lot of jeep/offroad guys.
I sell trailers for a living. Hopefully I can provide some insight.
The whole thing with hauling 2 vehicles (jeeps or not) is that its not about just the length of the vehicles. You need to be able to tie them down proficiently which means having room to anchor the tie downs ahead of the front axle and behind the rear axle. Also, the way the trailer tows behind the truck will be affected by where the weight is centered on the trailer. If you go too small then you will have a large amount of tongue weight or you will be forced to keep one of the jeeps resting behind the rear axle which will cause sway issues. I would look for something with a minimum of 30' deck length. Your truck will be fine to tow the rigs. Lots of manufacturers make 25'+5' trailers which means a 25' flat deck and a 5' beavertail. This should work just fine for you. Wilson you are correct.
I see it all the time with people trying to use the smallest trailer possible when it doesnt really benefit them to do so. A 26' trailer isnt going to tow any different and wont be that uch easier to maneuver than a 30' since they are both fairly large trailers.
Do yourself a favor and go with AT LEAST a 30' trailer if not larger. Make sure you examine the trailers GVW and dry weight in order to determine its tow capacity. The larger the trailer with the same GVW as a smaller trailer will be rated to tow less since it weighs more empty.