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Chris,
I am making assumptions that you have either towed very few or no trailers before. If I am incorrect or sound insulting, please accept my apologies for I do not mean to insult or belittle.
In general, make sure that the vehicle you are towing with can handle the type of trailer you use. Any trailer (state laws in most states) over 3,000 pounds total weight should have an electric brake sending unit in the towing vehicle that activates the brakes in the trailer as you brake. They are very cheap and very good insurance.
Most general purpose pick-ups and suvs are not equipped to handle a load above 5,000 pounds. This would, generally, mean that you would need a trailer weighing 2,300 pounds or less. Beefing up the springs in the rear (leaf springs) and installing a type III, IV, or V hitch on the back of your vehicle will help immensly. I do not like the load levelling hitches that force the towing vehicle and the trailer to be on the same plane. If you are hauling too much for the rear of the vehicle, you need a lighter load or a bigger vehicle.
Open aluminum trailers are fairly cheap, easy to find, easy to maintain, easy to pull, easy to stop, and last a long time. Metal trailers rust and are heavier. Enclosed trailers can be very, very hard to pull in winds. They are much more difficult to back and make it difficult to see. Enclosed trailers can provide additional covered parking for your vehicle. For what it is worth, I use the flatbed to pull the Porsche and leave my in-laws covered car hauler in the drive-way.
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David
'83 SC Targa (sold  ) MANLY babyblue honda '00 F250 7.3L (MINE!)
'15 F250 Gas (Her Baby) '95 993 (sold  )
I don't take scalps. I'm civilized like white man now, I shoot man in back.
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