You can order a new one from
the factory, if it's still in business, or from any sailmaker. Do not paint. The logos are printed on a treated, dacron type cloth that has an adhesive backing. After getting the logo lined up you remove the adhesive's paper covering and fix the insignia to the sail. I ordered a pair of red Catalina 27 logos, and two sets of black numbers, from the Catalina factory parts dept. They were delivered in a few days, cost was about $40. And....they look fabulous. I might suggest that if your logo is looking pretty ragged, it's possible that the sail holding it up is probably in pretty bad shape too. If you took it to a local loft, they might freshen up the sail and, at the same time put on the new insignias for you.