I've never had a good long term experience with an upgrade of any type. That 
being said you can't go from 32 bit to 64 bit
http://technet.microsoft.com/en-us/library/dd979563(WS.10).aspx

 John W. Cook
System Administrator
Partnership For Strong Families
5950 NW 1st Place
Gainesville, Fl 32607
Office (352) 244-1610
Cell     (352) 215-6944
MCSE, MCP+I, MCTS, CompTIA A+, N+, VSP4, VTSP4

From: Paul Hutchings [mailto:paul.hutchi...@mira.co.uk]
Sent: Tuesday, October 04, 2011 3:01 PM
To: NT System Admin Issues
Subject: Upgrading Windows in-place - your experiences?

I haven't upgraded a Windows Server install for years now as typically with 
physical boxes the box gets replaced after a three year period so the OS is 
rebuilt/refreshed.

Virtualisation has changed that somewhat as we now have VM's with a potentially 
infinite "physical" life, and as a result I have quite a few that are still 
running Windows 2003.

I may rebuild them all with 2008 R2 which also solves the fact that right now 
they're 32bit, but what are peoples experiences of upgrading Windows in-place?

As I said I've not had to do so for years now so I'm out of touch with how 
good/bad of an experience it is these days? The one potentially nice thing is 
that other than any third-party apps, the VM's are about as clean as you can 
get, no HP PSP or suchlike to have to deal with.

I should add we're talking small role-specific VM's here, nothing crazy like 
Exchange.

Thanks,
Paul
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