The systems and methods described herein relate to processing of information, data and automated transaction information involving content and/or experiences. In some exemplary implementations, illustrative automated methods of computerized information processing may involve automated auction processing, sweepstakes processing, handling, fulfillment and/or particular checkout processing of product(s) and/or item(s), including product(s) and/or item(s) such as experiences, physical products, digital products, and/or other offerings by luminaries. According to certain implementations, various product types, flag and/or identifiers are utilized in automated transformations of various purchasable products among the various offerings.