The only help I can provide and it is not much, have you reviewed the Codeplex project on msspatial extensions, which apparently exists because of 2005's ability to support Common Language Runtime objects..
http://www.codeplex.com/MsSqlSpatial
and this MSDN blog entry which professes to Demystifying Spatial Support in SQL Server 2008
http://blogs.msdn.com/rdoherty/archive/2007/10/28/demystifying-spatial-support-in-sql-server-2008.aspx
it has sample code for a application.
If everything seems to be going well, you have obviously overlooked something.
Ron
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