Subscriptions
Microsoft's Enterprise based agreements are basically subscription based models, and businesses have been using them for years. Back when I was responsible for Microsoft licensing for a large, international corporation, we sort of rolled in and out of Enterprise agreements, based on what it was we felt we needed to do. When a major upgrade was due (example - move to Windows XP from a mish-mash of earlier versions), it made sense to sign up for an Enterprise agreement, because it actually was a lot cheaper. However, we certainly did not feel it important to roll out every new major version that Microsoft rolled out. Enterprise agreements are typically three years, and there certainly was no guarantee that we'd renew when the three years was up.
However, it was basically a business decision. From a technical and support perspective, I have argued that we could have reduced support costs by keeping everything the same, and that usually meant up to date, on the desktop. Otherwise, there are costs associated with purchasing new PCs and imaging them with old versions of the O/S and Office, and also costs associated with having to support multiple versions. But, we were a chemical manufacturing company, not an Information or Financial company, and the bottom line was that the technical cost savings of an Enterprise agreement did not offset the cost of the licensing, compared to just going with the flow of a mixed environment where we'd keep a purchased system with it's licenses for five or more years. I have no idea how many companies keep a perpetual Enterprise licensing agreement with Microsoft, but it would be an interesting statistic to know...
Still, there are many examples of what I'd call subscription based licensing in the private sector. For all intents and purposes, cell phone, cable/satellite TV, and Internet services are subscription based, and/or heavily incentivized towards subscription-based "unlimited" service. I still do IT support as a hobby, but for all practical purposes I am retired and on a fixed income. Yet, much to my amazement each of my monthly bills for each of the aforementioned three services are near or over $100 apiece (my Internet is bundled with IP Telephone service). So, as a consumer, anyway, I've clearly "bought into" the subscription model, even when it ends up costing me more than I was paying pre-retirement. (Okay - I'm a Tech addict.)
When it comes to technology, it really does seem today we like having the latest and greatest, and are willing to pay for it even when the old one will still do the job it was intended for. I'm not so sure the same doesn't apply for software. It certainly does for anti-virus software. And budgeting is a funny thing - once you eke out a budget for something, it's so easy to just keep doing the same and "not have to worry about it".