Nearly anyone with a heavy and reliable pickup truck can make a reasonable amount of money by specializing in the pick up and delivery of boats. However, this is a much more specialized field than most would realize and will require some special preparations prior to a long haul, especially if the boat is on its own dedicated trailer.
First of all, one needs to make 100% sure that the boat trailer is legal and roadworthy. Due to the amount of time they are allowed to sit in one place, unused, trailer tires have a tendency to dry rot and if left unnoticed will lead to you being on the side of the road with a blowout and possible damage to both, boat and trailer.
Make sure the tie down straps are all solid and in good condition. This will keep the vessel from bouncing on the trailer and causing a great deal of damage if on rough roads.
Keep a transom saver with you to put on any boat especially with an outboard motor. This device is adjustable and supports the lower unit of the motor as such that any energy transferred from bouncing will go to the trailer rather than damaging the boat transom or the motor.
Make sure that the wheel bearings are well greased and keep a grease gun with you to re-lube them every 250 miles or so as this is likely the most common failure in transporting boats.
Be sure to use a hitch lock and make sure all of the locking mechanism works smooth as it should and that it is lubricated well.
Assure that all items inside and attached to the boat and trailer are well secured or stowed and that you have at least one spare tire.
Get your customer their new boat so they can get on the water and have fun!