My point was, you have SBS which has many built-in features that are very easy to implement. It sounds like you have manually re-configured these such as changing the pointer for My Documents to a share o the server. Also if you are using SBS defaults you would be using Exchange and there is no need to sync Outlook files.
SBS is not the same as server 2003, and is indented to be used with all defaults and in many cases the wizards MUST be used. If the computers are joined to the domain and the clients created, both using the server management wizards, then you simply click on the appropriate link in server management and choose redirect my documents. This will synchronize the local My Documents folder with the server during logon and logoff with the automatically created "users shared folders" folder. Thus the user while working is using the local copy. This also gives you an extra backup , local and server. You are correct this cannot be used for Outlook .pst files, but also it will not work for database files if that is an issue.
As for Outlook, using Exchange in cached mode (the default) maintains a copy of the e-mail on the server as well as a locally cached .ost file which can easily be converted to a .pst if needed for recovery, or when the network is not available.
Both of these are even more beneficial with a laptop as the files are always available when the network is or is not present.
I am not familiar with Cobian, but there are definitely many applications similar to Second Copy available. It is just the one I have used frequently, and therefore recommended.
