Update!
So one, @Craftplacer gets the gold medal for getting WLM 2009 past authentication and to the contact list! 
Two, I’ve been able to reproduce the same exact results with HOSTS entries of tkrdr.storage.msn.com and byrdr.omega.contacts.msn.com, since they don’t exist in the main program’s executable itself anymore, and I plan to get proper solutions for patching those services developed soon, and I think I know where to look…