Selecting the right plan is a key issue when moving to the cloud. When multiple applications need to be outsourced at the same time, the problem becomes more com- plicated, and different challenges might need to be solved. In this paper, we address this problem, characterize different outsourcing scenarios, and propose a brokerage- based approach that, depending on the specific scenario, is able to compute one (or more) ranking(s) over a set of candidate plans, based on how they satisfy the specific application requirements. Our approach is able to combine application requirements to determine a plan that is suitable for all applications, possibly taking into consider- ation their importance (differentiating the impact that their requirements should have in the selection process), and allows different stakeholders to express such impor- tance through linguistic variables, hence simplifying their definition and capturing the imprecision of human judgment.