ITunes Can Be Installed On 5 Devices - Why The Chaos When Reinstalling?

This comes to light on the very rare occasions I have to replace a hard drive, which unfortunately just occurred.  So obviously i had to reinstall everything, as I hadn't managed to clone the old drive before it failed.
I know that iTunes can be installed on up to 5 separate machines and currently I now have to installed on my secondary boot - Windows 7 Ultimate SP1.
I multi-boot as I test security software so like to have it installed on all my OS's.   It was my Vista Ultimate SP2 drive that failed.
Before I reinstall iTunes and Quicktime on Vista, is there some trick that I am missing that will negate the need for a complete re-download to that system of every single thing I've ever purchased?
If it's any help I keep the iTunes (Media) folder on my external drive - where it is totally independent of any operating system.   I don't use the Cloud for backups as I have restricted bandwidth and in any case am not paying for extra storage even if I had plenty of bandwidth.
Any tips and hints would be appreciated.
Forgive me if I should have read something or other - please point me wherever.

Did you use 'Software Update' to get the 10.8.2 update that is specific to the Late 2012 Mac mini?
If it is not being displayed, you may need to wait a few hours to use 'Software Update' to get this update, as the update that you need is currently not in the 'Support', 'Downloads' section of the Apple website.
This is the link to the update in the 'Support', 'Downloads' section of the Apple website, if you want to check back later: http://support.apple.com/kb/DL1603.

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