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We are running a version behind the latest for our ERP system which runs on SQL Server 2000. My version is not supported on 2008 (regular or R2). In fact, the latest version of the ERP is not certified to work with R2 (which isn't surprising since it hasn't been released yet)

I have done some preliminary testing with 2008 and it appears to work fine when run in 2000 compatibility mode.

My company wants to migrate to 2008 (either version) without upgrading to the latest version of our ERP system. I have a few questions:

Let's say I attempt to use my current ERP product in 2008 or 2008 R2. It's not supported. My biggest fear is that it will work, but we will notice a problem with it a few weeks down the road and then will be stuck. If that happens, is there a way to cleanly migrate backwards to 2000 or 2005?

What if I used a product like RedGate Data Compare and synchronized the data from the 2008 database back to the 2000? What do you think are the chances it would work?

If I went to 2008 and there was a problem after a few weeks, I think I could do an emergency upgrade to the latest version of the Vendor Product to be supported on that version. Any opinions about that?

I'm especially leery of migrating to 2008 R2 (in May) because my vendor does not yet offer a version to work with that and may not for many months. So, if I migrated to that and it failed in a few weeks, I'd have no choice but to try to go back.

I know I'm asking a lot of hypothetical questions, but I would appreciate your advice even if answers include phrases like "most likely it would...." and such.

What do you folks think?