@spenot thanks, this is very useful. We were planning to stick to an old-but-still-supported version at first and see how it goes. Fortunately we're starting with a fresh install and he keeps all his data remotely for access from different computers so wiping it again won't be a big deal, but thanks for pointing it out so I know what we're getting ourselves into.
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@gabrielesvelto Glad to be of help!
Keep in mind that a newer OS version may automatically change the format of things like the user's Photos or Mail database, so if those get synced to remote storage, you may be just as stuck on the new OS as if they had been stored locally