Also Sprach Stanley Barthfarkle :

b)-The small portion of the hull under the rollers isn't worth the risk of
damaging the boat or killing myself trying to block/reload it. It's probably
shiny enough as is, and the area in question is fairly small.

When painting a boat on a trailer, what I've always done is, after the
paint is dry, let out a foot or so of winch cable and roll the boat back a
foot or so on the trailer. Then paint the areas I couldn't get to because
of the rollers, let it dry, and crank the boat forward again.

I've also pulled boats off trailers onto blocks many times. The way I do
it is to build a well braced stand for the transom, and use cinderblocks
with a pad of wood for the keel. Put the blocks under the keel towards
the bow of the boat, and roll trailer forward while the transom of the
boat is kept in place by the transom stand. Eventually the bow blocks
will get in the way of one the the cross braces of the trailer. At that
point, you jack up the bow and move the bow blocks in back of the cross
brace. Repeat until trailer is removed.

Note, if you have a dog that likes to dig, keep him inside while the boat
is on blocks. My friend's 21' center console came very close to toppling
over because his dumbass yellow lab dug a hole under one of the blocks.

Dan

--
We're going to have the best-educated American people in the world.

-- Dan Quayle

(Well, someone's got to.)