To alleviate the workload of air traffic controllers, part of the air traffic may be handled by a future automated system. When deciding which flights to delegate, a distinction can be made between basic and non-basic flights, with the former being prime candidates for delegation. The human controller can then focus on the non-basic flights, where human competencies are most valuable and more difficult to automate. The classification of flights is preferably based on objective measures relating to the traffic situation. Existing complexity models are, however, often used for capacity predictions or airspace restructuring and primarily to assess the complexity of a sector as a whole. In this paper we use empirically collected flight complexity ratings from 15 professional en-route air traffic controllers. They indicated which other flights contributed to their complexity assessment of a single flight of interest. This exploratory study was able to build a machine-learning model which adequately classifies these flights, based on a qualified majority of controllers. By analyzing the interactions between the included flights, we discuss whether a classification model can differentiate between basic and non-basic flights, and which traffic features play the largest role. Once this can be done reliably and an appropriate complexity threshold has been chosen, a model can be developed as a starting point for an automatic allocation algorithm that distributes flights between a human controller and the computer.