Re: Painting top side of Livingston?
The answers to your questions lie in how far you want to go to restore the finish. If you are looking for a quick fix or an "easy" way to make it look good again I would recommend you take it to a shop.
You certainly can do it yourself. There are very durable marine paints on the market specifically designed for D.I.Y. However painting a boat correctly to get the best finish possible takes some work. Allot of work depending on your point of view.
You mentioned that the old paint is flaking off. It is likely that it will have to be removed before any new paint goes back on. That means stripping it or sanding it, probably both. Are you prepared to strip the old finish off? If so there are many high grade marine paints on the market that can be applied using a roller and a brush that yield a gelcoat-like smooth finish. But all that shine requires good prep work to make it look its best.
Roll on marine paints are not as complicated as automotive paints and you do not need specialized equipment to apply it. But marine paints can be just as involved as auto paint when it comes to prepping. A good paint job is 90% prep 10% paint.
If you are willing to do the work the result is certainly worth what it takes to get it done right.