I think in some sense he's like the dream spiritual father. He was fairly pastorally-sensitive, yet could be stern and direct when necessary. He tried to reach people where they were, for example translating works into the local language rather than insisting that people learn Greek/Latin. He could have lived as luxuriously as he wanted (after he got to Constantinople anyway), but lived a modest lifestyle. He was capable of great sermons, yet focused not on his own ideas or speculations so much as discussing what Scripture said. He wrote a lot of stuff on Scripture, which later authors (e.g. St. Theophylact) apparently thought worthy of following closely. He actually did have some good theological stuff to say (e.g. on gender, anthropology, etc.), but it was often layered with practical ideas and scriptural interpretation. His liturgy is still used (if in modified form), whether because it is superior or not I don't know. Also, he did not want to be a clergyman, but eventually agreed to it (in other words, he didn't want to be a clergyman for fame, power, etc.).