After being a one man shop for far too long, my new cohort and myself have experienced the joy of actually validating that the Compact Framework projects in Subversion are acually correct. The Solution has a Lib solution folder which contains all of the external dependencies needed for the project to build and run. On a clean machine it appears that the Compact Framework 2.0 is not installed when you install VS2008. This led me to put mscorlib, System.Windows.Forms, etc. into the Lib folder to save Dan from needing to install VS 2005 (which he has blogged about) in order to get the assemblies we need. Oddly enough, all UserControl and Form classes in the solution do not appear to have designer support when the solution is checked out, getting a clean local copy shows the same behavior for me. Controls just display all their designer-added children (Label, Button, etc) in a giant Control tray.
The only thing that seemed to resolve this issue for us is removing our Lib assembly references and re-adding the fundamental dependencies from the GAC. This makes one wonder: what bizarre implementation detail of the designer support causes this issue?