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rather easily i would think. my '86 tows the 700# tent camper with no problems at all. what engine, transmission, and gears are in your '88?
and i'd go ahead and get a 4x8 trailer as it would handle standard 2x4's, sheets of plywood, etc., better. i use one of the ones from Harbor Freight. not the folding one, but the one with the 1700 pounds capacity. use it for everything too big to fit in my short bed ranger: riding mowers, atv, cement blocks, etc. and the price is only about $400 at their local store. takes about half a day to build it. here is teh link to the one i have:
http://www.harborfreight.com/automo...-12-inch-five-lug-wheels-and-tires-94564.html
just remembered... you really want to get a frame mounted hitch receiver. best bang for the buck. the bumpers really aren't the safest bet for towing no matter with the owners manual says about 200# on the ball and 2,000# gross trailer wt. on the bumper.
i can't answer that question, 1) i have no idea where you live and 2) i have no idea what the laws are like in your area