As far as spinnakers go, that's a tricky thing to carry out well and I don't know what kind of paint holds up well on the spinnaker. I have seem some that are applied with a "sharpie" permanent ink marker where you can use an old projector to project the image on the spinnaker and color it in...takes a while though!
I think Mike Krantz has this figured out. They ran a giant Zhik logo on their spinnaker in the '09 Tybee. When I asked how it was done he said they spray painted it - And when I looked closely there was some bleed. I'm interested in experimenting with this, but need a spin that is not preimpregnated with silicon, and has not had the seal and glide treatment (or sail kote).
