The Jeep and trailer do fine. It helps with the trailer being narrower than the TJ when threading through trees and rocks (the track width of the trailer is the same as my Willys). The trailer is based off a little Harbor Freight 4' trailer frame (heavily modified). The tub at the base is only 40" x 50". Read all about it here (very long thread):
Link:
Mini Harbor Freight (type) Trailer Ultimate Build-Up Thread - JeepForum.com
As I'm sure you're aware, these little Wranglers don't have much room inside for gear (even with the back seat removed). Even with my lil' trailer being on the small side, there's just so much more stuff you can take with you in (or on outside) a little trailer like this. I may be doing the WABDR this summer right after the NWOR. I'm thinking of taking the Willys and trailer on that one. And there's even les room for gear in the Willys compared to the TJ, so thank goodness for the trailer.
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Here's a video of the Jeep TJ and trailer in action:
(207) TJ and trailer - YouTube
And one more thing - you'll be amazed at what a gear change will do for your YJ. I'm running 4.88 gears with 33" tires on my TJ, but I've got the 2.5 four-cylinder engine. With the 4.0 six, usually 4.10 gears work well with 31" tires, and 4.56 gears work well with 33" tires. You'll not only get your fifth gear back to where you can use it, but you'll really like having the lower gears when starting out in first gear (especially on the trail starting an uphill climb).