Matt Hamilton discusses five aspects he loves about Plone, including its strong community, buildout deployment, ZODB for object persistence, Diazo theming capabilities, and the use of Python. He also mentions five frustrations, such as legacy code, outdated documentation, inefficiencies in the catalog, unclear quality evolution, and the slow consensus-based decision-making process inherent in its democratic structure. Overall, he highlights both the strengths and challenges of working with Plone.