Migration from SBS 2003 to 2008 Standard

I am working for a company that has SBS 2003 which is running Exchange and SQL Server on the one box. I am planning to upgrade to 2008 standard, SQL server 2008 and Exchange 2003 all on separate boxes. I have the transition packs so that I can re-use the CALs. I dont know upgrading the single server with these as if it goes pear shaped will help, since I might be stuck with no back out plan apart from a restore, which I dont want to use. So, my plan is to add a new 2008 server to the domain and promote to DC, then add the other new servers. The questions that I have is, are there any problems transferring Licensing Server Service from SBS, I have found that it could be problematic? After when the 2008 server is promoted, does that mean that the Licensing is taken over by the new DC and the 75 user limit not longer exists? Will I be able to add the DC only and still run exchange and SQL on the original box, so that I can do an upgrade?

Did you try to go from SBS 2003 to SBS 2008 Pre which would give you the products you are looking for and SBS 2008 Premium includes SQL 2008 and a second Windows Server license for a second box. But if you do want to move away from SBS, then conside looking at SBSmigration website for some options.

Thanks for the reply, we are at 75 now and want to increase as are about to expand with more staff and the server is creaking at the seams. I checked out the SBSmigration website and it only tells about SBS 2003 rather than 2008 standard. Are you sure that it will work in the same way with 2008 or will there be any kind of problems? Thanks.

I think that transitioned SBS CALs do not cover access to Server 2008 and the Non transitioned SBS CALs cover Server 2008 access until May 2009. You might have to but CALs for 2008 incase you want to use the transition pack for, that will also cover the Windows, Exchange, and SQL Server products. Its better to contact your License Reseller or MS Licensing for conformation and some more information.