I can't speak for MS's plan but Adobe CC is far from "wringing even more cash" from their user base.
That depends on your point of view.
We use various parts of Creative Suite occasionally for work, but not as everyday software. We bought a copy of one of the bundle versions more than four years ago, for a one-time price of about £1,250 at the time.
Today, it looks like the closest equivalent UK pricing on Creative Cloud is about £560/year. It would have cost us approximately twice as much so far under the new pricing model, and we'd still be locked into paying forever.
Defenders of the model talk about the benefits of paying a small fee monthly being more manageable, but I'm running a business and can add up, so accounting over the course of a year is hardly a burden.
Defenders of the model also talk about all the improvements Adobe make and the benefits of having the latest software, but if their improvements were worth much to us then we'd have bought an upgrade to CS6 and we never saw anything to justify the cost. I haven't seen much to got me excited in any of the applications we use ever since the move to Creative Cloud either; there's plenty that we would pay for, but either Adobe aren't doing those things or they aren't very good at advertising when they have.
The thing is, even if they did those things now, while we'd have happily paid for the upgrades on a one-time basis, there is zero chance that we're going to commit to unregulated rent-seeking on software we rely on to do our business. We have seriously considered spending significantly more money to get a high-spec Mac just so we can run some of the generation of graphics software that is emerging on that platform, sometimes costing less for a permanent licence that CC does for a single month, yet with a reputation that suggests it would be at least as good for the kind of work we do if not better.
I think our attitude to Windows payments would be similar. Give us decent optional upgrades at sensible intervals and we'll happily pay a reasonable price for that support. Try to lock us in so something we already paid for switches off if we don't keep paying, and we'll never buy Windows again, and just stick with our existing Win7 licenses until we move entirely to Mac and Linux machines.