Here is my 2 cents worth since I have the large graphic. Per Dave Posey, of Posey Sails, man I miss him but you can't work forever. The best material is what they call insignia or number cloth. It is sailcloth with a sticky backing. I’ve never had it come off. I’ve also used the Mylar or plastic and have it come off. The Palm Tree on my sail is insignia cloth (not sure what I used as a pattern for the leafs). The sun is plastic and had it peel once. My sail is monofilament so I’m guessing plastic sticks better to it then it would to regular type sails. I used a little water under it to slide the sun around some then a squeegee and that worked all right. I was sailing several hours after applying it, just the time to drive to the beach and rig the boat.
If you have access to a sail maker try to get the insignia cloth. I made the pattern out of construction paper. All you have to do is flip it for the other side. If you look on my website you can how large the graphic is and how it looks.
Mike Shappell
If applying vinyl graphics to a mylar sail, try not to use application fluid - rather apply them dry. If you have to use application fluid, give them at least 48 hours to dry and rub them down again after that period before using them.
I own a vinyl graphics business and I've used a LOT of vinyl graphics on sails. Only once did I have any come off....but that one was "sanded" off the sail as it was beached on it's side and I'm not sure much of anything would prevent that!