And what an interesting process it was. The two vendors I contacted
looked at me like I was out of my mind while I explained what was
needed. (Many people consider me out of my mind- but most have more
reason to reach that conclusion then either of these vendors had). In
both cases I knew just exactly when the "Aha!" moment occurred and the
two disconnected suppliers realized how one simple step would solve a
problem that has long afflicted owners of boats with bright transoms
and quarterboards.

The problem: Boaters applying vinyl letters to quarterboards ("name
boards" in some circles) and other brightwork find it very difficult to
maintain the finish on the brightwork without screwing up the vinly
letters as the years go by. It's good pactice to do at least a
scuff-down sand even on brightwork in sound condition and add a couple
of coats of varnish each year.
Applying varnish over the top of existing vinyl letters tends to "lift"
the edges and that will lead to failure within a few seasons. Masking
off the letters and sanding the spaces in between can be ridiculously
tedious, particularly with a complex font.

The solution: Apply the vinyl letters to a very thin sheet of
transparent plastic, cut to the shape of the quarterboard, and then
fasten the plastic sheet to the quarterboard. The wood finish below
shows through. When the board needs varnish, the plastic sheet with the
letters can be unscrewed, set aside, and then reinstalled when the
varnish has set. Under normal circumstances, the vinyl letters will
last about 10 years (maybe less in a climate where they are subjected
to intense UV exposure), but there is no way to get that sort of life
from the letters if trying to refinish around them every year.

The cost: $7.50 for two pieces of plastic at Tap Plastics, plus the
labor to shape the plastic to match the curve of the quarterboard.
(Could probably have done this myself with a jigsaw and the proper
blade, but labor to shape both was only another $22 so I saved the time
and bother).

When I showed up, (plastic in hand). at the firm that does the vast
majority of boat graphics in the area, they didn't initially understand
the concept. They thought I was going to apply the new letters directly
to the teak, and then cover the letters with the clear plastic to
protect the wood.
One comment was, "The letters might not be quite as readable as you
want if they're under a sheet of plastic." No, no......the letters go
on the plastic and then the plastic goes on the wood.
"OH! That's a great idea! I can't remember anybody doing it like that
before!"

My transom lettering will go onto the new paint, so no plastic overlay
needed there. There won't be a need to renew the paint every year like
there's a need to renew the varnish. However, the same concept would
likely work very well with vinyl lettering on a bright transom.