> See the account books for Stirling Castle circa 1467 for a dole of food to two gypsies.

That would certainly push things back a few decades. Do you have a source?

Not sure about the 1439 charter, though. I've found Ramage's article, in Notes and Queries of 15 January 1876 (at archive.com - it's in series 5 volume 5). All he says there about the charter is that in it Halliday "wadsetts" various lands, including "the Tynklers land" to the Laird of Mousewald. It seems to be Ramage himself who makes the connection to the fact that "Faas, Kennedys, etc." are known in later times to have lived near to the place mentioned in the document. He raises the possibility that this and other references to "tinklers" going back to the late 12th-early 13th century, might indicate an earlier Gypsy presence in Scotland, but doesn't prove that they do.