Hi Sandra,
I've been following your saga here with some horror because this story of contacts/calendar sync is much more confusing that we had hoped. You've got multiple contacts stores, multiple calendars, and multiple sync technologies all working at the same time. You seem to have hit the perfect storm.
One question I'm not sure I have gleaned from your posts so far... you are using multiple user accounts (aka Live IDs), right? So, you sign into Office Live Small Business with emailaddress1, click sync to Outlook from your contacts, fill in your user name and password again and then sync your contacts to Outlook. Then sign out of Office Live, and do the whole thing over again with emailaddress2? Everything seemed to work fine, but then later they stop syncing?
This may not be the cause, but when you first sync your contacts into Outlook and you are prompted for your user name and password, did you click the checkbox to remember your account credentials? If you did, this may be storing your credentials into Office/Windows. If that happens, Outlook may be remembering only one or the other of the two sets of credentials that you entered.
If you are still stumped on this, you might try this:
Note: if you're on a Windows 2003 Server machine, you can do this by navigating to Control Panel --> Stored User Names and Passwords.
Now, start over again, but when you sync your contacts, make sure NOT to check the checkbox that says 'remember' these credentials when Outlook prompts you for your user name and password.
We have a similar issue when using multiple sets of credentials with SharePoint Designer, another Office application that works with Office Live. Here's a discussion about that on our developer forum.
Hope this helps.
Chris
Chris Beiter
Program Manager, Office Live Small Business
http://blogs.msdn.com/cbeiter/