It depends on your hardware.
If you have everything Intel based then yeah, it almost just works, except the i915 driver occasionally has huge regressions, Mesa sometimes has huge regressions, and the kernel itself oftentimes has huge regressions.
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Run Debian Stable or CentOS and you won't have to worry about "regressions" for at least 2 years. If the hardware works when the system is installed or upgraded, it will work for the lifetime of that release (barring exceptional bugs).
Windows has nothing comparable, besides the LTSB/LTSC releases that people can't even figure out how to get legally.