Transforming a diagnostic technique into a monitoring product imposes a large number of challenges, both known and unknown. This paper will discuss a number of the known technical challenges that has been encountered in our history, like considerations on system properties, sensors, platform choice and algorithm design. To detect the unknown challenges as early as possible, field prototypes and pilots are needed and considerations on those are discussed.The paper ends by discussing some aspects of monitoring applications that we have designed in the past in light of the presented challenges.