Not that I agree, but the FSF's issue with non-free software does not seem to be purely based on those who sell proprietary software lying (or being unclear) about the limitations, but at least partially on the fact that they even offer such "raw deals" to begin with.
Given that Microsoft has long published the support lifecycles for its major products, and that those support lifecycles are often guaranteed (as much as anything in the commercial world can be) many years into the future, any criticism on this score just feels like bad faith.
The alternative is to take your chances with free software where outside of any commercial support agreement with a specific provider you generally have no actionable guarantees of any kind that your support will last as far as the time your installation completes.
Yes, you're right, in the end is the users fault as they didn't foresee those consequences and some didn't even made migration plans, even when stated clearly.
You can even argue that all of the things there end up being the users fault as they choose so for convenience.