This dissertation discusses strategies I have used for interpreting and learning The Crutchof Memory and The wreck of former boundaries by Aaron Cassidy in preparing them for studio recordings. These scores both utilize unique and complex tablature notations which necessitate thorough interpretive engagement and advanced learning strategies from the performer. This study details my musical interpretations of the works and learning strategies I employed to both navigate their complexity and heighten my interpretations in recording. It then analyzes my recordings, reflecting on which strategies realized my musical interpretations and identifying areas in which to employ strategies for further development of my relationships with the works.