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I wouldn't bother with a 2wd. If nothing else, a 4wd will be easier to sell some day. Aside from that, a 2wd is liable to have trouble pulling a heavy trailer (and you WILL load that sucker up from time to time). I recently pulled a heavy trailer with my 4wd Yamaha Big Bear 400 and had a hell of a time until I realized I had it in 2wd. Even in 4wd I had some trouble getting up a hill. Of course, all those ruts, tree branches, wash-outs, and patches of loose dirt didn't help!
Point is it takes a whole lot more traction to pull a trailer when the ground is uneven or there's any kind of depression or obstacle like a branch or something the trailer tire has to climb over or out of. It won't take much to make you wish for a 4wd.
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