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"But small organizations typically dont have access to the expertise needed to create disk images or push managed system updates. Many small organizations dont choose to purchase these consulting services, either."

I submit small companies without IT resources or the financial assets to hire them most likely don't have the expertise to move to the web either. I further submit the acquiring the expertise to create and deploy system images is cheaper than getting / buying the skills necessary to migrate to the web (especially if you already own the server, Windows clients, and software).