You can migrate from SBS 2003 to SBS 2011 if you can find the installation media and license keys. That would be best. There is no reason to go to SBS 2008 instead of SBS2011 -- SBS 2011 runs on Windows 2008 R2, while SBS 2008 runs on Windows 2008. There is no compatibility reason to choose SBS 2008.
If you are looking for what current product to upgrade to, it depends on whether you need to run Exchange on the new server. If you do, then you should get Windows 2012 R2 and use HyperV to host two VMs, one for the DC/fileserver role, and one to run Exchange 2013. If you do not need Exchange, then you should purchase Windows 2012 Essentials. That assumes that you have 25 or less users.
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