The ability to understand simple vocabulary, conveyed by haptics, has demonstrated encouraging results, even with limited training. However, the level of achievable accuracy on communication indicative of real-world conversations, typically characterized by long phrases formed by complex vocabulary, remains unknown. This work presents an in-depth quantitative and qualitative analysis of the learning path of one experienced participant over a two-month period of daily practice with our vibrotactile communication system. By the end of the two months, this participant was able to correctly identify 97% of the words in phrases consisting of 6-8 words, delivered as a sequence of vibration patterns. We compare the progress of this individual with three naive participants who practiced on single-word identification, discussing the subjective aspects of haptic communication, such as the cognitive process of decoding words, and the need for personalization, both in the training program and the haptic encoding.