Commercial databases compete for market share, which is composed of not only net-new sales to those purchasing a database for the first time, but also competitive "win-backs" and migrations. Database migration, or the act of moving both application code and its underlying database platform from one database to another, presents a serious administrative and application development challenge fraught with large manual costs. Migration is typically a high cost effort due to incompatibilities between database platforms. Incompatibilities are caused most often by product specific extensions to language support, procedural logic, DDL, and administrative interfaces. The migration evaluation is the first step in any competitive database migration process. Historically this has been a manual process, with the high costs and subjective results. This has led us to reexamine traditional practices and explore an automatic, innovative solution. We have designed and implemented the Migration Evaluation and Enablement Tool for DB2 for Linux Unix and Windows, or MEET DB2, a tool for automatically evaluating database migration projects. Encapsulated in a simple one-click interface, MEET DB2 is able to provide detailed evaluation of migration complexity based on its deep analysis on the source database. In this paper, we present MEET DB2, and discuss many aspects of our design, and report measurements from real-world use cases. In particular, we show a novel way to use XML and XQuery in this domain for better extensibility and interoperability. We have evaluated MEET DB2 on 18 source code samples, covering nearly 1 million lines of code. The utility has provided benefits in several dimensions including: dramatically reduced time for evaluation, consistency, improved accuracy over human analysis, improved reporting, reduced skill requirements for migration analysis, and clear analytics for product planning.