You may have the trailer in too far unless it is a steep ramp. With the guide ons being that low, when loading the boat onto the trailer, they will get caught under the hull to deck joint in the rear causing damage. Suggestion is to put temp. longer ones on as the others come off easily. If the ramp is at a normal slant, then you may be in too far. Try not putting it in so far.
One other thing. When you go 10-20 miles, it is a good point to pull over and check tie downs, winch strap and most important the hubs. If they are warm you are fine but if super hot, you have problems with the bearings/racers or it could be if you have brakes being stuck in a locked position which either will require immediate attention. Suggest that you carry a small grease gun, extra tire, four way lug wrench and a floor jack with a couple of blocks of wood.
One other thing. When you go 10-20 miles, it is a good point to pull over and check tie downs, winch strap and most important the hubs. If they are warm you are fine but if super hot, you have problems with the bearings/racers or it could be if you have brakes being stuck in a locked position which either will require immediate attention. Suggest that you carry a small grease gun, extra tire, four way lug wrench and a floor jack with a couple of blocks of wood.