Hull damage
First off, I’m really more interested in having fun with the boat and actually sailing it than making this thing look perfect. The hull deformations don’t really bother me as much as the leak… I’d like to be able to leave it on our mooring for a week or two without worrying that it’s going to take on enough water to sink. (I also have a couple of bilge pumps and solar panels, so I can rig those up as well, but I would prefer to figure out the leaks on their own. When I first put the boat in the water it would take on about 2-4 inches of water per hour. That was when I found the crack in the hull where one of the bunks had actually pressed in enough to create a crack in the hull. I did a quick fix on that last summer and got the boat to the point where it would only take on a couple of inches of water over night. The location of the two deformations and the crack is right under the quarter berths (where I can't see it). My tentative plan is to sand the hull, re-epoxy/fiberglass the cracked area, and then paint the hull. A more involved idea I had was to cut large access holes in the quarter berth, build some reinforcing structure in there to repair the hull shape, repair the leak from the inside with fiberglass, fill with fresh floatation foam, and re-fiberglass the quarter berths. Sounds like a lot of work that might be a later project!
Hull and deck paint
As far as hull paint, I have been reading everything I can on the Mariner forums and on Nate B's Orion website. I do think that I am going to repaint the hull and deck this summer. It sounds there are a lot of options for paints. I am thinking I will try the roll and tip method of application. For the deck, I have a lot of the usual spider cracks. I am not sure if a thorough sanding and painting will take care of that for a couple of years, or should I consider a more involved approach with grinding out the cracks and filling them.