Telehealth services for long-term monitoring of chronically ill patients are becoming more and more common, leading to huge amounts of data collected by patients and healthcare professionals each day. While most of these data are structured, some information, especially concerning the communication between the stakeholders, is typically stored as unstructured free-texts. This paper outlines the differences in analyzing free-texts from the heart failure telehealth network HerzMobil as compared to the diabetes telehealth network DiabMemory. A total of 3,739 free-text notes from HerzMobil and 228,109 notes from DiabMemory, both written in German, were analyzed. A pre-existing, regular expression based algorithm developed for heart failure free-texts was adapted to cover also the diabetes scenario. The resulting algorithm was validated with a subset of 200 notes that were annotated by three scientists, achieving an accuracy of 92.62%. When applying the algorithm to heart failure and diabetes texts, we found various similarities but also several differences concerning the content. As a consequence, specific requirements for the algorithm were identified.