This book chapter examines complexity of attributes affecting the online purchasing process in tourism and hospitality. Eight elements (i.e. marketing activities, perceived benefits, perceived risks, over-choice confusion, price issues, quality issues, consumer trust and intention to purchase) are identified as of principal importance. Based on a sample of 735 holidaymakers, the empirical findings stress the role of perceived benefits in e-marketing activities; the significance of perceived risks for price and quality issues; and the importance of over-choice confusion to e-shopping. The research employs Qualitative Comparative Analysis (QCA), an innovative technique in tourism. QCA results are compared to regression highlighting the possible superiority of this non-linear mixed method against correlational analysis. The book chapter also progresses from fit to predictive validity, something that only a handful of studies have employed in tourism and hospitality, and generally in the service sector. It also discusses several theoretical, methodological and managerial implications, whilst it contributes in both, theoretical and methodological domains