I suppose my point is that it wasn't how proprietary software tended to work until relatively recently. For many years, we (assorted small businesses) were using the Pro editions of Windows with no drama. This only became an issue when Microsoft chose to make the Pro edition of Windows 10 unsuitable for professional use (in our humble opinion) while simultaneously locking the more suitable editions behind Big Organisation Hassle.
As a direct result of that decision, they have essentially lost our business, just like certain other large software organisations whose names start with A that have adopted similar customer-hostile practices in recent years. There are viable alternatives for almost anything these days when you're a small business with the flexibility to make intelligent policy decisions about your hardware and software purchases on a case by case basis and, if appropriate, to change those policies however you want later on.
I've been pretty displeased with how Microsoft has chosen to alienate Customers the last few years. I've made a good since the late 90's installing and support Microsoft software in small businesses, and the changes in the last few years, particularly with Windows 10 and the associated Server versions, have been distressing.
I will say that I've never found the Open License program to be a tremendous hassle. There was good cost savings to be had using transferable licenses, and the product use rights and other terms and conditions were clearly spelled-out. Dealing with resellers was the worst part of it, but I managed to find good resellers who would mostly just do what I asked for and not hound me with sales-gerbil nonsense. The volume license management website was actually fairly nice, and was useful for keeping track of a Customer's license inventory.
I've had a hard time getting much free/open-source software adoption in my small business Customers. They almost always have a mission-critical application that keeps them locked to Windows (or SQL Server, Office, Exchange, etc), and no budget or desire to finance software development. The value proposition of spending money on the proprietary software is often just good enough to make it worth the cost and draconian licensing.
As a direct result of that decision, they have essentially lost our business, just like certain other large software organisations whose names start with A that have adopted similar customer-hostile practices in recent years. There are viable alternatives for almost anything these days when you're a small business with the flexibility to make intelligent policy decisions about your hardware and software purchases on a case by case basis and, if appropriate, to change those policies however you want later on.