It might not matter if users like their products, so long as OEMs and corporate / school IT managers like them.

Practically speaking, people only need to like products enough to be able to tolerate them, even if they're gritting their teeth in anger the whole time they use them. Many people end up buying things they hate because they don't really have any better options (e.g. virtually every telco, cable company, or ISP). Microsoft would have to intentionally make Windows completely broken, meaning so broken it's very difficult to get even basic applications to run and stay running, before the switching costs would be justified (that is, before people would stop buying it).

In a theoretical world, consumers are free to simply buy whatever they like, and their purchases directly reflect their intent to reward the company that made the product they're buying. In the real world, there is lock-in, there are exclusive vendors, there is employer mandate and inflexible custom processes with dependencies, there are other forces that make it so you almost have to buy certain things. Windows is definitely one of those things that many users feel they practically have to buy, whether they like it or not.

Every vendor of computer products (hardware or software) is trying to achieve this lock-in effect, because it means a lot of easy money, a much more stable and less sensitive income stream.

Sure. With Debian, you can choose NOT to update it.

Also, every app, every website, every .... ;-)