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To address that last paragraph, I don't believe it is anything special about Linux. I know a business that still keeps a small army of Windows 2000 servers in virtual machines due to software that simply won't run in any newer version (not even Windows 2003, despite being the last NT 5.x, it's just incompatible enough).

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We've had bad experiences mixing Office 32bit vs 64bit applications. Also with Microsoft Windows Server 2000 just double check the license agreement and software licenses some of them have caveats of running the software within a Virtual Machine.

I know Oracle licenses we had to have a dedicated machine because they charge per core/thread.

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