This document discusses a project to migrate 350 websites and 50,000 pages from an old CMS to a new bespoke CMS at the University of Edinburgh. It describes three common dilemmas faced in large migrations: 1) whether to start from the top or bottom of the site, 2) how to engage users while meeting deadlines, and 3) whether to finish the new CMS before migrating content. For each dilemma, considerations are presented and groups discuss potential solutions. The document emphasizes community engagement, phased approaches, and testing new systems in parallel to address challenges of large-scale migrations.