Landscape sustainability aims to consistently provide long-term, landscape-specific ecosystem services. The concept of nature’s contributions to people (NCP), broader than that of ecosystem services, has sparked methodological controversy regarding the new assessment framework of NCP. Accordingly, for further exploration of the essence of landscape sustainability, a way forward in better assessing NCP that differs from previous assessments of ecosystem service is necessary. Five key issues for assessing NCP are summarized in this paper, including: 1) how to determine generalized or landscape-specific parameters; 2) how to identify different people’s needs from a landscape; 3) how to deal with the complexity of non-material NCP at landscape scale; 4) how to evaluate the relationship between different NCP from a landscape; and 5) how to assess landscape multifunctionality based on NCP. The way to deal with these key issues is discussed, including: determining generalized or landscape-specific parameters based on research targets; tracking nature’s contributions to different people’s needs considering spatial flow; forming new spatial data for non-material NCP; evaluating the relationship between different NCP depending on threshold of benefit; and assessing landscape multifunctionality based on the relations of NCP.