It's two different business models: Simplicity versus Total Solution. Starting from scratch simplicity usually seems better, but as companies grow they (for good financial reasons) wind up doing a lot of 1 off solutions in the name of flexibility and being customer-centric.

I agree. I wonder if they appreciate how frustrating it is to deal with their licensing. Even more than price, small IT departments want to just get out from under that wet blanket. Why Software Assurance? It's all to Microsoft's benefit. If a company wants to upgrade then let them pay the discounted price and upgrade on their own schedule. Don't turn it into an annuity for the vendor.