Unfortunately, this should be a very straightforward process.  As I'm sure some are aware, Microsoft has structured their System.Data.Linq object model such that this is a colossal pain to implement in practice.

I have a prototype DotNetNuke DataContext adapter that supports the attributed model while at the same time supporting DNN objectQualifier and databaseOwner customized at runtime.  I believe that it will allow development using the normal Linq to Sql designers without any of the commandline generation nonsense, and make module deployment a non-event. 

I am looking for a few technically sophisticated module developers who are interested in testing out my prototype before I deploy it to a wider audience.  Interested parties may contact me at bhaynes [a.t] fas [d0t] harvard [d] edu.

Brandon