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My current customer did a study of portal / content management systems (CMS) to replace their existing system. I read their reports and felt compelled to do a little googling and study myself. I haven't used a CMS before for any real application development, I have been to presentations about SiteCore and I have experimented with Umbraco and Sharepoint but that is about it. I think CMS systems can be a great tool for building portal / content sites with limited functionality but when the system your are meant to build is leaning more to an application with rich functionality my instinct is that most CMS systems add to much complexity and friction.