My numbers looked like that YEARS ago. I tried rubber cement, but that just slightly delayed the inevitable. My numbers still kept coming off. When four of my five number had come off, for 2 years I had the sail number "1". I don't think anyone believed I owned the very first Hobie.
When the sun is right, you can still see my numbers in glue residue. I did price out new numbers a few years back, but at $8.00 a pop, I figured 10 numbers at $80.00, plus tax; -that could buy a lot of beer.
I'm not sure of the best process to put on new numbers, so they don't fall off right away. I would guess, it would be wise to use a rag dampened with mineral spirits, to clean the glue residue, then dry, before applying the new numbers. -Would that damage the dacron's coating? Even if it did, sails that old probably have the coating damaged from wear.
One thing I've wondered about: Is it possible to dye the numbers on the sail? Black Magic Marker???
Maybe it's best to play taps to your numbers, and move on in life as a numberless wanderer.