I have a l985 Hunter 31 that is a good boat and I will keep it for a long time. I take good care of it, stay on top of maintenance, and hope to eventually do some coastal cruising up and down the East Coast in the next five years. My efforts, related to the outside hull and topsides, have included a fair amount of gelcoat and some topside "softspot" repairs, and a little minor hull repair. I intend on 2 part epoxy painting ( either Awlgrip or Imron)on the topsides and hull in the next year or so. I am familiar with various spray, brush and roll painting techniques,so in a year or so, I will paint the hull. I have painted the deckskid on the topsides a 2 part grey already and it looks beautiful. There are a few prep steps that are essential to do thoroughly, the boat needs to be protected from the elements which can be accomplished with a temporary structure of wood frame and plastic, and using a high volumn, low pressure spray gun on topsides, and a regular cup gun on the hull, can result in a very professional, classy paint job. I think it is very doable if you love your boat enough to want to invest lots of labor(to save money), be patient with the process and practice first, research the prep details, and set up the week or so to do it, it is absolutely worth it. I would love to have a new Hunter but I don't have the extra money, and more important to me, I love to sail my boat, my wife loves it, and we are adding things we want to enjoy the boat, but most of all, I just love to look at the lines of this model and it gives me what I need (not always want but thats OK) Go for it- painting can definitely be an option.