> Vast majority of uses of cal apply to dates > 1900 (and I'd say a significant amount is > 2000)
According to what? Your use?
> 'cal 16' should require a flag saying "Yes, I know what I'm doing, this is the actual year" and/or print the corresponding year for this century (being explicit, when printing, to which year it refers to)
The command wants a year number as input. '16 is an ambiguous abbreviation that gains meaning only within context. As the command can't ask you what you meant, the default behaviour is sane.