Licensing regime will survive
For me, Microsoft's licensing regime will survive for as long as there are people deploying complex, on-premises enterprise systems. A per user/per month subscription model does not work well enough in that scenario. Both the vendor and vendee need the flexibility that comes from complexity. If you need to push through a multimillion dollar deal, you need something more nuanced than just "multiple the number of users you have by 'x'".
Over time I think we'll see more SaaS-type deployments sold on a subscription basis, but this has more to do with outsourcing compute power and maintenance to the cloud rather than any inherent benefit in subscription licensing.
Of course, SaaS has an ancillary benefit of making sure that users have the latest and greatest -- i.e. the most well-patched, most secure and safest. That's a good thing for everyone.
Licensing reform is overdue
Microsoft's licensing schema is far too complex for most companies to manage. Microsoft has an estimated 500 to 1,000 employees who work in product licensing. That points to a system that requires far too much overhead to maintain. It's inefficient for Microsoft and it's near impossible for businesses to comply with the convoluted licensing for operating systems, servers and applications.
The Office 2013 backlash that Jason referred to in the debate is an example of how the Microsoft licensing plan begs for reform. In fact, once Microsoft recovers from the Office 2013 licensing change and the launch of Office 365, I'm hoping that they launch the Great Licensing Reform of 2014.
SaaS-style applications such as Office 365 should help resolve licensing issues for Microsoft's customers. A subscription pay-as-you-use model is good for customers and for Microsoft alike. Customers will benefit from being untethered to a single computing device. Additionally, the upfront cost to businesses will be easier to manage. Instead of spending a huge lump of cash for software licenses, businesses can ease into a payment plan of sorts with predictable recurring subscription costs.
For Microsoft, a reformed licensing model creates a more honest customer count and, in turn, would generate more revenue for Microsoft because this type of software use would be impossible to pirate. The SaaS and subscription models work for other businesses such as Salesforce.com, Google and VMware. It's a proven system. Customers like it and so do vendors. License management for both parties is simple.
Change isn't easy but it's time that Microsoft follows this trend that has almost left them behind.