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You can update Debian many years later. I just updated a system over multiple versions no problem.

Yes, you can upgrade after several years. But you can't skip a version. If you started at 8, you need to upgrade to 9 and then to 10. Can't skip 9.

Sure, but all versions of Debian are still available so I don't see why that is a problem... Except as an annoyance due to the extra work.

I had packages just gone on enough occasion s.