According to the documentation site (http://msdn.microsoft.com/en-us/library/azure/ee924680.aspx) the latest versions are due to expire on the 11th of January with the new versions being enabled on the 5th January. I guess that means a lot of people will have to spend their first week back at work testing the new os release in the 5 working days before the existing guest oses are retired.
On any sufficiently complex team project you will eventually need to find a way to keep the developer machines (and the build servers) aligned.
The web platform installer is a great way of getting started on this.
Now the webpi also has a command line version that must be run as admin.
The following will list the software that you have installed:
webpicmd /list /listoption:installed
Then you can build a script similar to the following:
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This with a bit of testing can give you a full machine setup for say your CI servers without requiring complex maintenance.
This is before you have to write a single script!