One of the things you look for when hiring a pro is experience. I don't want my boat to be someone's training ground. I haven't got all my quotes yet, but I figure it's going to cost a bundle. At least twice what a monohull of equivalent length would cost. But the boat needs to be properly maintained if its going to keep its value, and (considering total cost of ownership is determined only after the boat is sold) it's got to be done right. There's no savings in the end if this becomes one of those jobs that only looks good from 30+ feet away.
Once the mast is off, it only takes about an hour or two to dismount the floats. They could bring the center hull inside for painting, then bring in the floats and support them inverted for a better working angle. I estimate each float weighs about 3-400 pounds so handling won't be difficult.
Next question is color -- for ease of maintenance I'm considering a white that closely matches the gelcoat of the deck. White shows imperfections and salt less than colors.... although I might go for a light silver-gray or even stars and stripes blue.