Abstract: A computerized property inspection and work order creation system is disclosed, where the system automatically provides proposed work performance transactions to the user based upon prior inspections, work orders, proposed work performance transactions, and executed work performance transactions. The work performance transactions can include sending quote requests or orders to suppliers or sub-contractors, creating and sending work orders to staff members for completion, generating charges to property owners, and updating budgets based upon the inspection and suggested items and services. The proposed work performance transactions optionally are provided by an artificial intelligence engine.