I go where I'm towed.
One thing about towing that people might not think about is that the published towing capacity of a vehicle is really only a starting point. A little bit under doesn't mean you're necessarily okay. The trailer being towed, windage, wheelbase and weight distribution of the towing vehicle, tires, brake set-up, terrain and altitude, and weather will all have their say.
In general, you can get away with bumping your limit when moving a tow a few blocks to a boat ramp with moderate slope and good traction whereas you want to have a huge amount of reserve capacity for towing cross-country through mountains, weather, traffic, etc.
Overhead power poles are of course a sinister threat. Trailer tires generally need quite a lot more pressure than car tires, so check frequently. Protect tires from sun damage. And don't forget to be sure to have your hitch ball and coupler match, lock your coupler, and cross your chains. For a big cross-country trip, I could see wisdom in having pre-greased and bagged spare wheel bearings.
We once had a power outage at our lake cabin when someone towed a sailboat away from the lake -- until they encountered their first overhead powerline, which knocked the boat off the trailer.
We once know someone who tried to tow about 7500 lbs. with a 3500 lb. capacity towing vehicle. It sort of worked -- until they got to the first downhill and the trailer decided to pass them. Fortunately, the body damage that resulted was to the Cherokee and not to any people.