I'm planning on painting my trailer over the winter, unless my boat happens to sell before then (i doubt it will). I have some rock chips that drive me nuts. My plan is to use plastic sheeting and tape off anything i dont want paint on. It'll require me to do some crawling around but i don't think it should be bad. I was planning on trying using spray paint and see how it comes out. I've seen a few redneck paint jobs on vehicles over the years that i never would have guessed were spraypaint, so i know its possible to do a good job. I can always sand and repaint if it turns out like crap.
I'm interested to see or hear what others have done and how it turned out.