To sort of get back to the OPs question. Towing load behind a riding mower can put a lot fo stress on the machine. Even the small trailers can actually hold a lot of weight. If you property is pretty much flat, you might be ok with a lower end model, such as those found at the big box stores. But if you want a machine to last a long time, you'll need to step up a bit. I would start at the JD X3xx, Simplicity Broodmore or equivalent. The JD X5xx models, or equivalent from Simplicity etc are pretty stout, and I wouldn't worry about them at all. They will last a good long time. Going crazy like some of us, isn't necessary, but it is fun!
My trailer hold a bit more than a cubic yard of material, and has a weight capacity around 1 ton. I am spreading mulch in the pic, but I have filled it heaping with firewood, and it does great behind my machine.
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