I'll agree with the above. We were looking at the 27BESS, but ended up buying a 29QBSS. That 34' of trailer (tongue to bumper) really pushed around my Ram 1500 until I started adding additional anti-sway bars, and reducing weight. As it is, I recall they were around the same weight dry, but my trailer's about 900 lbs on the tongue, which with me being at 240, doesn't leave room in my 1150 payload for the rest of the family.
I make do, and try to adjust my driving accordingly, but I'm anxiously waiting for the day that the budget's right to trade up this truck to something bigger.
Since you just recently traded to the Jeep, you're not going to want to switch that any time soon, so I'd recommend looking for a smaller trailer.
You could try PMing DDC. I believe he pulls his rig with a Jeep and can provide some real world experiences around it.
There's no use crying over spilled milk, unless it's on your keyboard.