I've been lurking here (learning and planning) for a couple of years. I began collecting components and building my century/touring bike early last year. Last December, a colleague and I went on an S24O; 45 miles each way to a State Park. I took my commuter bike and the combination of rear rack, panniers, and strapping my tent to the handlebars was fine. That was a good experience.
Next in the plan was a three-day/two-night mini-tour: 52 miles on Friday to Bankhead National Forest; 45 miles on Saturday to Dismals Canyon; and 80 miles home on Sunday.
I had recently completed my new bike, based on a Surly Cross-check frame. I did not have racks for this bike yet, so I borrowed a B.O.B. Yak from a friend who had done the Natchez Trace a few years back.
The first 40 or so miles was fine. The bike was performing perfectly and I didn't find the trailer to be much of a concern. However, the last 8-10 miles to the campsite was on gravel roads and I was definitely not prepared for that. (Lesson 1.) My 700x28 tires did not feel stable enough. But the trailer turned out to be downright frightening on the gravel descents. (Lesson 2.) Ascents weren't all that great since my rear tire woudl lose traction on the steep sections so I had to walk a couple of climbs. My colleague with full racks and panniers seemed to be much more stable than me. Regardless, we made it to the camp site and had a good night's rest.
The next day started out on pavement with a really nice climb, but we soon hit gravel again. After about five miles, we stopped at a map to try to find a better route out of the forest. When turning around and starting back to the road, I got my wheel into a rut, started heading down a ravine, slammed on my brakes, and this brought the trailer up off the ground and then dumped me over to the right. What seemed like a minor, low-speed incident soon became a big deal as it bent my derailleur hanger and bent/broke the derailleur such that it would no longer engage the b-adjustment and the derailleur body was pulled forward to the chainstay.
We ended up having to call in a wife with a van to extract us; the tour busted.
I had read enough on the forums to know that some people found the B.O.B. trailers squirrelly on fast downhills and I was prepared to mitigate that. However, I was not prepared for how unstable it felt on gravel on even mild descents.
Oh, well. Several lessons have been learned and that is the point of these mini-tours. I'll be doing all my future touring using racks and panniers in the future. And I'll definitely do more to avoid gravel (e.g. trade more miles for pavement) or set out with fatter tires.
I've appreciated learning from all the experience and advice on this forum. Hopefully, someone will learn from my brief experience as well.