Most trailer sailors know that pulling a boat down the road can be complicated. The boat has to stay on the trailer and everything associated with the trailer and the load has to be as good as it can be. What we sometimes forget is the load has to be checked often. Every fuel or rest stop, we check the boat for it's position on the trailer and that the tie downs are tight and not loose. We check the boat to make sure that nothing is coming off the boat. When you pull the boat for the first time, extra caution is required to make sure everything is right with your trailer and boat.
Winch straps that are new or that have been reposition will draw tight as you drive down the road. When the strap become loose, it will jerk the trailer eye and cause some interior damage to the eye installation. A block of soft wood is placed inside the boat as a spacer. The nuts and washers will embed themselves in the wood causing the eye to move forward on the outside. On a Com-Pac 16, the glass in the hull's bow is 3/4 inch thick. The nuts and washers will not go through the small holes in the glass.
A safety chain at the winch stand will keep a boat on the trailer if you have a winch failure. It will not solve the jerk problem above. A good 1/2-line tie-tie between the boat's eye and the winch stand is a good idea. It needs to be tight to solve both problems.
While you are trailering down the road, if the trailer and boat swings from side to side behind your car, the trailer doesn't have enough tongue weight. It is easy enough to loosen he winch stand and move it forward and then pull the boat forward with the winch.
Trailer wheel bearings are precision devices. Loose, damaged or bearings that lack lubrication will fail. I consider bearings that go long distances without failure good bearings. You can check your bearings without removing the assembly by jacking the trailer up and rotating the wheel. If it rotates smoothly and moves a small amount from top to bottom, the bearings are good and adjusted correctly. For those people that wear suspenders and a belt, disassemble the bearings, clean the bearings and replace the grease seal. Make sure you leave the bearings a little loose to handle heat expansion
I recently had a customer that jerked his trailer eye over a long distance. He was concerned that the eye compressing the wood might be catastrophic. When boats are laid up, the glass at the bow is overlapped to make sure that this part of the bow is strong and rigid. You can see by the picture below, trailer eyes are strong.