Leave the fuel line attached to your motor and prime the motor (squeeze the bulb) before trailering a boat. The gas in the carburetor stops the float from (literally) banging during trailering. The banging float can damage a pin and a sleeve and subsequently cause the carburetor to flood at low speeds.
Also we use a transom saver for long trips and over rough roads. This supports half the weight of the motor to the frame of the trailer.
Do not overload the trailer.
Check the weight bearing capacity of the trailer tires. An old trailer
could have weak springs. We learned that the hard way one year. The
springs sagged and allowed the tire to rub on the fender causing a
blowout. Make sure there is adequate clearance between the trailer fender and the tires. Error on the side of safety here.
Check the wheel bearings of your trailer before the trip. Make sure there is adequate grease. Repack the bearings if any water is present.
We always check the tires of the trailer for heat at every stop. We also bring a 12 volt air pump and a can of tire seal, just in case. Never neglect to bring a spare tire for the trailer.