I've been really thinking about a trailer for a few years now, might be pulling the trigger soon. Main 'tow rig' will be a Road King. Depending on how it handles a trailer I might someday get a hitch for my Sportster and/or FJR, but I doubt it. I just don't know about it. Guys say they can't tell it's back there, and reviews say they like it, but I'm still nervous about hooking to a loaded trailer and heading out. Traveling with the girlfriend on the back would be way easier, as we nearly always camp and sometimes go on an actual vacation, meaning stay in the same spot for a few days. Vacation trips involve normal vacation packing. Clothes, hair drier, make-up, kitchen sink, etc.
One of the biggest things that worries me is the trailer hitting a pothole with one tire and starting to sway, I'm not sure how a bike would react to that. I've felt sway with a truck, it's not fun at all. It was an extreme example of an overloaded truck and trailer, but it almost put me on the roof. Truck was sliding sideways and all I could do was hang on. Smaller examples have happened to me, notable the trailer hitting a bump and starting to bounce while hooked to a smaller tow rig. My dually doesn't care what's back there, but I've towed with my Lincoln town car and it's pretty noticeable. Heavy car, soft suspension. I'd imagine tuning the trailer suspension to a specific load would help, maybe with some added shocks or something.
I'd be looking to loosely follow this build: