I\'m sure this is a common problem, but I can\'t find much info about it.
I have a work computer, a home computer, a surface, and maybe some Azure VMs th
There's something called the "User State Migration Tool" that is intended for preserving state in corporate PC desktop deployments for wipe-and-load, similar to your Azure scenario.
If you know something about the way the extension settings are saved (as shown in the blog), it's not too hard to construct an XML descriptor and use the deployment tool to apply the settings. The tool is command line so it is easily automated.
http://technet.microsoft.com/en-us/library/hh825142.aspx
This solution has increasing value when you have more than just Visual Studio to migrate into your VM.