>Purchasing/licensing software is always a hassle. Even aside from the monetary cost, you need to decide which to buy, go through the purchase process, and sometimes you also have some activation hassle.
This. Navigating MS licensing is an absolute headache inducing time vampire for smaller organizations.
What I hear you saying is: "There could/should be a better way to do it". Adding ", hmmmmmmmmmmmmm...." to the end of that statement may be of some use to you or others, financially.
The problem is that this is really an internal problem at Microsoft. They have so many licensing programs targeted at different industries that even trying to figure out who you need to be talking to can be a nightmare. Sometimes you'll be directed to a program like BizSpark, sometimes you have to go through a reseller like CDW, some industries have specific third-party programs that make the most sense, e.g. TechSoup for non-profits.
Navigating MS licensing is the software equivalent of navigating the US tax code. Why would you willfully subject yourself to that when you could be getting things done?
This. Navigating MS licensing is an absolute headache inducing time vampire for smaller organizations.