Re: Painting Boat and Trailer
Need to know the size of the boat and do you have a roller trailer? We used to take our 16' Starcrafts off the trailer in the yard every year to paint the bottom. Raise the tongue, let it roll off so the stern is on the grass, lift the bow and pull the trailer out. Reverse the process with the winch to put it back on. Takes a few people. Be mindful of the lower unit.
If you have bunks only, maybe slide some dowels for rollers between the hull and bunk and roll off?
There are elaborate plans for jacknig the boat up and building braces under it and pullnig the trailer out. Having a boat propped up while you are working around (or under) it is scary.
One of the simplest ways to lift part of the boat off the trailer is to use the tongue jack and blocks. For example, lower the bow (raises the stern) block the stern, raise the bow and the stern part of the trailer lowers under the blocked stern. But be careful and chock your wheels!
Lift your boat off with a sling or lines on the stern cleats and bow eye but don't leave it dangling as the weight can warp a hull after time. This is not a good idea for heavy boats, obviously.