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Someone who owned 10,000 hardcover books and the same number of vinyl records could bequeath them to descendants, but legal experts say passing on iTunes and Kindle libraries would be much more complicated. … Most digital content exists in a legal black hole. “The law is light years away from catching up with the types of assets we have in the 21st Century,” says Wheatley-Liss. In recent years, Connecticut, Rhode Island, Indiana, Oklahoma and Idaho passed laws to allow executors and relatives access to email and social networking accounts of those who’ve died, but the regulations don’t cover digital files purchased.