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Does either Rackspace or AWS provide APIs for billing information?
The value add of Cloudability is that you don't scrape the portal -- they do. It's a little better now than when Cloudability was first introduced. You used to have to give them the admin credentials for your whole cloud account. Not cool, because what's to stop them from launching a dozen servers? But then Rackspace Cloud added better security granularity. You can now create a "Billing Only" user and give those credentials to Cloudability, instead.
Multiple Realms and Multiple TGTs under MIT Kerberos for Windows
I updated my original question which hopefully explains how resources know which ticket/key pair to use.