The 2 server part of the problem has more to do with the default way Samba is setup on SME servers and not to do with being on different sides of a VPN.
Here I am talking generic Samba. nothing specific to SME. (folks, please correct me if need be).
By default in M$ terms you are running 2 Win2K Servers as standalone, not as domain controllers or part of a domain, just 2 servers in a workgroup. Just as with M$ servers you would need an ID/PW on each to authenticate and use resources. (In fact in Win9x/Me the IDs and PW would need to be identical, since Win9x/Me cannot logon as more then 1 user at a time.)
But wait you say, Samba can act as a domain contoller, so why can one be the domain controller and the other just a server in the domain or a backup controller? Well in Samba they can (one be a PDC and the other be a server on the domain that is), but each user still needs a linux ID on the box since the Samba IDs get mapped to Linux IDs for filesystem security. There is some new stuff coming (winbind) that will do away with the need for Linux IDs, but I think it's still pretty experiemental.
I assume the typical mass Samba server deployment uses something like NIS to replicate Linux users across all systems, then a Samba domain controller to cooridinate Windows users logins, but at this point I'm talking past my experience.
The remote annouce stuff I mentioned for Network Neighborhood should be pretty easy to add as a SME template for Samba, see samba.org for the syntax and the document here on modifing SME templates if need be.
The users will be the real challenge. I see 2 options:
1) For a low number of users. Set them up on both servers and show them how to change their passwords on each to keep them in sync.
2) Check the archives and ask around if there is a way to either synchronize the users between the systems or make the addition of a user on one system trigger the addition of the user on the other. This sounds scarey to me.
Sorry for no straight forward answer. I suggest doing a lot of reading on Samba to get a comfort level with it.
- Todd