Doran:
Before I moved into a Honda Element, I owned a series of new 4 wheel drive Jeep vehicles, maybe 8 in all. It started with a 2 door Cherokee in 1990 with a 4.0 liter and ended with a 2005 Grand Cherokee Limited with 330 hp hemi. Somewhere in the middle of the run, I reverted back to a 4.0 liter straight six in a Grand Cherokee. (I was usually buying the 4.7 liter V8.) All the while, I was towing a Glastron 237 SL Futura w/270 mag mercruiser I/O (22' 7")with double axle trailer with brakes. Estimated the weight at 5600 lbs.
The 4.0 liter in my 2 door Cherokee was rated to tow 5,000 lbs. The same with a Grand Cherokee 4 door.
The 4.0 liter is a tough engine and should serve the purpose well for your son. Likely, since your looking at a 2 wheel drive, the chance that it was off-road driven is remote. You can always locate the former owner and find out if it was used for towing. Most of them are driven by women who never have towed a thing.
The Mustang might look like fun, but your insurance agent might not be able to insure a 16 year old in a sports car. The Jeep has more steel and weight to it, and therefore have some safety advantage over a small unibody sedan.
Red harped on the trailer brake issue, and that issue applies to all trailers and all vehicles used for towing. There should be a law in the USA that requires brakes on any trailer rated over 1000 lbs. A Honda Element has poor brakes for trailering. But with disc brakes on the boat trailer, I can't be happier with the 2.5 liter 4 cylinder Honda AWD to tow 3500 lbs. (19CSS). Your next project should be to put disc brakes on your recently re-habilitated trailer.
