As pjmlp mentioned below bigger orgs have better Microsoft licensing deals - volume licenses and such and smaller ones can apply for Bizspark or whatever to get

As pjmlp mentioned below bigger orgs have better Microsoft licensing deals - volume licenses and such and smaller ones can apply for Bizspark or whatever to get lower prices. But yeah your point still stands that they should simplify the licensing for people who are neither big org nor a small startup. Especially so in the wake of cloud and Linux.