Thanks for your suggestions. I looked the log file and see the following crashes (see below), although I am not certain these were the crashes I talked about since I have had also some other crashes. Please note that I did switch TFS projects with the task board.
The good news is, it stopped crashing after my bug report and we even did a successful sprint planning meeting with it, so until it starts crashing again, let's not investigate any further unless you see something in the log that concerns you.
2010-01-18 11:14:01,303 [17800] [1] INFO IRC.Gear.WorkItemManager.Wpf.App - Application Starting.
2010-01-18 11:14:20,325 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=False, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=1, Warnings=0.
2010-01-18 11:14:20,668 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.Planning.IterationPlanningSession - Could not find iteration planning session file for Tensing Mobile Platform. (C:\Users\mvandillen\Documents\Work Item Manager\srv-denali\Tensing Mobile Platform\IterationPlanningSession.xml).
2010-01-18 11:14:20,914 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=True, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=0, Warnings=0.
2010-01-18 11:14:38,856 [17800] [1] INFO IRC.Gear.WorkItemManager.Common.TfsConnection - Cache Refreshed: False || Num Tries: 3 || Server: srv-denali.
2010-01-18 11:14:45,036 [17800] [3] INFO IRC.Gear.WorkItemManager.Common.UserSettings - User Settings file changed (C:\Users\mvandillen\Documents\Work Item Manager\UserSettings.xml).
2010-01-18 11:14:45,969 [17800] [3] INFO IRC.Gear.WorkItemManager.Common.UserSettings - User Settings file changed (C:\Users\mvandillen\Documents\Work Item Manager\UserSettings.xml).
2010-01-18 11:14:55,624 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=False, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=1, Warnings=0.
2010-01-18 11:17:50,175 [17800] [1] DEBUG IRC.Gear.WorkItemManager.Common.TfsAssemblyLoader - Looking for assembly 'Microsoft.TeamFoundation.WorkItemTracking.Controls' in the VS2008 directory.
2010-01-18 11:17:50,178 [17800] [1] DEBUG IRC.Gear.WorkItemManager.Common.TfsAssemblyLoader - Attempting to load assembly 'c:\Program Files\Microsoft Visual Studio 9.0\Common7\IDE\PrivateAssemblies\Microsoft.TeamFoundation.WorkItemTracking.Controls.dll'.
2010-01-18 11:17:50,261 [17800] [1] DEBUG IRC.Gear.WorkItemManager.Common.TfsAssemblyLoader - Successfully loaded assembly 'c:\Program Files\Microsoft Visual Studio 9.0\Common7\IDE\PrivateAssemblies\Microsoft.TeamFoundation.WorkItemTracking.Controls.dll'.
2010-01-18 11:18:39,462 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=False, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=1, Warnings=0.
2010-01-18 11:19:53,461 [17800] [1] ERROR IRC.Gear.WorkItemManager.Data.SourceControlManager - Error connecting to source control server srv-denali for project Product Backlog Request. Microsoft.TeamFoundation.VersionControl.Client.VersionControlException: There is no team project named 'Product Backlog Request' in source control.
at Microsoft.TeamFoundation.VersionControl.Client.VersionControlServer.GetTeamProject(String name)
at IRC.Gear.WorkItemManager.Data.SourceControlManager.Initialize(String serverAddress, String projectName, Nullable`1 useSourceControl)
2010-01-18 11:19:53,617 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.Planning.IterationPlanningSession - Could not find iteration planning session file for Product Backlog Request. (C:\Users\mvandillen\Documents\Work Item Manager\srv-denali\Product Backlog Request\IterationPlanningSession.xml).
2010-01-18 11:20:24,008 [17800] [1] ERROR IRC.Gear.WorkItemManager.Controls.SetCurrentIterationWindow - Error saving Project Metadata for Product Backlog Request. System.NullReferenceException: Object reference not set to an instance of an object.
at IRC.Gear.WorkItemManager.Data.Metadata.ProjectMetadata.SetCurrentIteration(String currentIterationPath, DateTime startDate, Double duration)
at IRC.Gear.WorkItemManager.Controls.SetCurrentIterationWindow.Save()
2010-01-18 11:22:19,989 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=False, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=1, Warnings=0.
2010-01-18 11:22:20,004 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.Planning.IterationPlanningSession - Could not find iteration planning session file for Tensing Mobile Platform. (C:\Users\mvandillen\Documents\Work Item Manager\srv-denali\Tensing Mobile Platform\IterationPlanningSession.xml).
2010-01-18 11:22:20,133 [17800] [1] INFO IRC.Gear.WorkItemManager.Data.SourceControlManager - Source Control Get Result (Tensing Mobile Platform): No Action Needed=True, Resolvable Warnings=False, Conflicts=0, Failures=0, Operations=0, Warnings=0.
2010-01-18 11:22:25,637 [17800] [1] ERROR IRC.Gear.WorkItemManager.Data.SourceControlManager - Error connecting to source control server srv-denali for project Product Backlog Request. Microsoft.TeamFoundation.VersionControl.Client.VersionControlException: There is no team project named 'Product Backlog Request' in source control.
at Microsoft.TeamFoundation.VersionControl.Client.VersionControlServer.GetTeamProject(String name)
at IRC.Gear.WorkItemManager.Data.SourceControlManager.Initialize(String serverAddress, String projectName, Nullable`1 useSourceControl)