When I mentioned upgrade I was thinking that Microsoft would give us software discount going from SBS2000 to SBS2008 and not migrating any settings. We would put 2008 on a new server as a clean install, get the bugs worked out, copy over our project files and disonnect our old server.
Found out that our software (Autocad Civil 3D) may require a database server in the future so I am back to leaning towards SBS2008. Especially if Microsoft will give us an upgrade price break, since SBS is only about $600 more for us than Server. Plus after reading "end-of-discussion-absolutely-not-hosting-email-internally issue" quote I realized how long never is.
SBS2000-SBS2003-SBS2008 sounds good but it doesn't appear that we can go the software assurance route unless we hire someone to do the install and we like to be in control of our own destiny. This is probably foolish but the only problems we have had in the past were ISA and Exchange related.
Thanks
Mark
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