The present application relates generally to systems, software and electronic commerce. More specifically, systems, methods and software to reconcile free-text with structured data are disclosed. Structured data may be in the form, for example, of a set of attributes designated as associated with an occupiable property. Free-text may be parsed and one or more terms, words, phrases or the like may be extracted by the parsing and compared with the structured data to determine if there is a difference between the structured data and the free-text it is compared with. Detected differences may be reported (e.g., to an endpoint) in real-time or near real-time and may include a suggestion or recommendation to change the free-text to more closely match the structured data or to change the structured data to more closely match the free-text, or both, for example. An endpoint may be a client device such as a smartphone, tablet, pad, or the like.