Another Thoght
My neighbor buddy, Gary, fresh from living most of his life in Erie PA came over and said this would work. paint as much as you can reach while on the trailer. use cinder blocks bridging two 2x6's piled on top of each other as support, after raising the tongue as high as possible (even if you have to use a car jack) then lowering the trailer carefully, paint the foreward part above the bunks, then do the aft part the same way. Hope this helps. PS- the boat won't roll because the stern is still sitting on the bunks.