re: Easiest way to repaint the deck?
"Whats the easiest way to paint the deck?"
Hoist a big plastic curtain around the boat, haul a couple of paint grenades halfway up the mast, one forward, one aft side. Set off the grenades, don't walk on the deck until the new paint has dried.
What, you've never used a paint grenade? (G)
If you REALLY want to do it right, and never regret the way you've done it, painting a deck means removing every last piece of hardware because no matter how carefully you mask around them--you'll see masking lines afterwards. If you can live with that, a good masking job still takes a very long time.
Also be aware that regular masking tape binds up to things really nasty after a few days, the blue stuff takes a bit longer, and there's special silver tape from 3M that won't stick even if it is in the hot sun for 30 days.
No matter which way you choose--the prep is the key. Scrub the deck, clean it, make sure all the cracks dry out. If you remove hardware, that's also the time to check rebedding on every piece which again makes the job longer but also makes sure there are no leaks.
Shortcuts? Yeah, the paint grenades. (G)