A WOMAN, who has been charged repeatedly with pestering American talk show host David Letterman since 1988, was arrested after police found her sleeping near tennis courts on his property. Margaret Ray, 41, who gave police an address in Crawford, Colorado, was arrested after police received a complaint of a trespasser. It was Ray's eighth arrest for alleged trespassing on Letterman's property or breaking into his house in New Canaan, Connecticut. She was charged with first-degree criminal trespass. Ray's visits to Letterman's home began in 1988, when she was caught driving his Porsche. She was sentenced to six months in prison in June 1992 for trespassing. In May, she left a book on meditation and a letter in Letterman's driveway. She also has spent time in a state psychiatric hospital for bothering the celebrity.