I've towed a 8 1/2 x 20ft flat front trailer tens of thousands of miles with a 99' F-150 truck. My longest trip was So Cal to North Carolina and back, carrying a race car in both directions (6-days round trip.)
The truck is rated to 8500lbs with a weight distribution hitch, and the trailer weighed in at approx 6500Lbs loaded. I later purchase a 8 1/2 by 24ft that weighed about 9000lbs fully loaded, this was undoubtedly too much for this truck.
In addition, I have towed a 8 x 20ft camper with my Tacoma V-6. (Towed round-trip, SLC Utah to Yellowstone.) The trailer weighed in at approx 5000 lbs loaded (for camping) and the Tacoma is rated to tow 5500lbs. Fuel mileage was approx 10-11mpg. No problem on the flat land and gentle hills, but the more severe inclines significantly reduced my speeds. Also, I did not use mirror extensions as I am so accustom to towing and backing up trailers, I find them unnecessary.
The trick to towing is using the engine in it's proper power band and not straining the transmission. When towing on hills, drop a gear and use more RPM. This will help put the engine in a higher power band and reduce the heat in the transmission caused from torque converter slippage. Also, don't tow on any up-hill grades and/or headwinds in overdrive. On most vehicles, overdrive reduces the amount of trans oil passing through the cooler and increases trans temps. Also, make sure your tow vehicle is outfitted with a class-III hitch or greater and a secondary trans cooler to keep the trans from experiencing premature failure. (Here is a link that covers actual hitch class vs. weight capacity.
http://www.etrailer.com/faq-hitchclasses.aspx ) My F-150 currently has over 80K miles towing and 180K total miles. And, I am still on the original engine and transmission.
Fuel mileage is is not only effected by the frontal area of your trailer, but also with how efficient your engine is. You will obtain greater fuel mileage keeping the engine in its optimum power curve over lugging the engine up a hill. It takes the same amount of horsepower regardless of rpm's. So, if your engine is stressing to tow the load up a grade at low rpm's, drop a gear and bring the rpm's up to a more efficient power band. This will reduce stress on the engine and increase efficiency based on the given load.
Also, keep the load distributed properly. I have seen more accidents on the highway related to improper loading more than any other cause. (Second greatest cause outside of lack of driver talent/experience is trailer brake related (improper adjustment and/or failure to properly control brakes based on braking force requirement at the time.) And, as mentioned above, an anti-sway (sway controller) is recommended for any trailers of this size.
Regarding trailer brakes, as others have pointed out, it is a must have item. But admittedly, I totally dislike all the inertia activated brake controllers. They are slow to respond, they are in consistent and greatly effected by road incline. I have a brake controller that unfortunately is no longer manufactured. It was designed and patented by a retired engineer and when he passed, the family sold the patent to one of the inertia style manufacturers. Unfortunately the new company has chosen to no-longer manufacture this controller. I think they just wanted it off the market as it was less profitable to sell. Rather than use inertia to activate the brakes, this controller used brake pedal position to control the trailer braking force. This method insures proper braking force regardless of terrain and/or incline. Knowing this device is no longer available, if I was to have to replace the unit, I would only purchase a controller that works through monitoring of actual tow vehicle brake pressure. TV brake pressure is the most accurate method of determining the braking force requirement for any given trailer.
Also, I believe somewhere on this website is a link that shows the difference in coefficient of drag for the differing frontal configurations. Very informative numbers and I will consider them in purchasing my next trailer.