anyone have a suggestion as to best way to bottom paint a grady 208 on a bunk trailer.
Pulling the trailer out from underneath the boat is pretty easy with a small boat - but you still need to take your time and double check your cribbing as you go, of course. I don't know your skill set, but to give you an idea, someone that's had experience with this can do it less than an hour. Paint where you expect to put cribbing, let it dry for a few days, then pull the trailer out. The spots you'd use are the two aft, corner chines and under the bow keel, where it is still horizontal. A solid surface to put the cribbing on is important.
When placing cement blocks, use two at a time at the aft corners, rotating each layer 90*. You'll likely need two layers of 2 blocks, then a final layer of a single block. Make sure that any wood you use is oriented such that the grain is perpendicular to the bow keel - it IS possible that the bow keel can split the wood if the grain is parrallel to it.
Your other option is paint what you can. Let it dry. Then jack the boat off the bunks enough to let the boat lean to one side. Paint. Let dry. Push the boat over to the over bunk and paint. Secure the boat in each position so it doesn't accidentally tilt over on you.