I had an email from a friend recently asking about a licensing question pertaining to Microsoft. It reminded me of how much I dislike trying to understand their various licenses and as far as I know there's not a place where you go and say "I want to do this in this configuration, put in writing what licenses it will take for me to be legal". I swear I'd pay $50 to get the occasional answer on a piece of Microsoft letterhead. We would all rather be in compliance and I think in small to medium sized companies we just do the best we can, and save a little money for a rainy day in case we got it wrong and get audited/found not quite compliant.
On the same topic, trying to manage those licenses (Microsoft plus other vendors) is something I dread. A friend at a company I used to work for asking me if I knew where the license was for a particular piece of software. I had authorized and paid the license fee some years earlier, but who knows where that license was? At the office I've got big envelope full of various receipts, licenses, box tops, etc, that I hope will convince that some day auditor that I really did pay for what we're using.
Maybe it's not simple, or can't be simplified? I just wish it was easier to understand the right thing and to keep track of doing the right thing (all licenses the same size of paper!).