Disclosed are systems, methods, and media having at least one processor; and a non-transitory computer-readable medium storing instruction which, when executed by the at least one processor, cause the at least one processor to perform operations comprising receiving from one or more sources images related to a plurality of features of housing offerings, said images being associated with other images related to features of housing offerings; presenting to a first user an initial prompt and based on response to that initial prompt, presenting a plurality of selectable images related to a first feature of housing offerings; receiving from the first user input regarding the desirability of the images related to the first feature of housing offerings; and iteratively deriving, based on inputs regarding the desirability of the images related to one or more of the plurality of features of housing offerings, a hypothesis regarding a different feature of housing offerings; based at least in part on the hypothesis, presenting to the first user images related to the different feature of housing offerings; and receiving from the first user input regarding the desirability of the images related to the different feature of housing offerings.