Upgrade from SQL 2000 SP4 to SQL 2008 R2

I currently have a machine running SQL 2000 SP4 on Windows 2003 SP2 (32-bit). I want to upgrade an end up running SQL 2008 R2 on Windows 2008 R2.
Looking at the documentation as to what is supported, it seems like the upgrade path would be as follows:
1. Upgrade SQL to 2008 R2 in-place. I believe I would need to do this first since SQL 2000 SP4 is not supported on Windows 2003 so I cannot upgrade the operating system first.
2. Upgrade Windows to 2008 R2 in-place.

Has anyone done this? If so, what are the gotchas I should know about?
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Julian123Asked:
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Dave BaldwinFixer of ProblemsCommented:
Windows 2008 R2 is 64-bit only.  Will your hardware support it?  The drivers for applications will also have to be upgraded.
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Julian123Author Commented:
Sorry, I meant Windows 2008, the 32 bit version, not 2008 R2.
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Brian ChanDBACommented:
Can't do side-by-side upgrade?
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Dave BaldwinFixer of ProblemsCommented:
I was wondering about that too.  For my own use, I never 'upgrade' a machine to another OS, I get a new machine to put it on and transfer my files and programs over.
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Aaron TomoskySD-WAN SimplifiedCommented:
Agreed on never upgrading an os. Id also suggest skipping 2008 (vista based) and goin right to 2008 r2 ( win 7 based) if you don't have problems with having a 64bit os.

If you go this route, I would install SQL express on another box and try to import the database files. You can also connect to the sql2k db from the 2008r2 express ssms and make a backup that way. This way you can deal with SQL separately from the os.
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Brian ChanDBACommented:
Sometime it may be tough on budget or other limitation and that's understandable to be tempted to do it in-place. But, if you are doing it to a critial produciton environment, it is a clean cut to do it side-by-side as you still have the option to backout. Keep that in mind, MS is not going to be responsible for your data.
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