Agree Gareth - if this is implemented in the end, I think managing those expectations and ensuring that users do see it David's/Tim's way will be essential - if 2 of the 4 respondents just in this thread so far, as people involved in plugin development, see that potential confusion, then how much more is that going to happen with 'ordinary' site admins?
I can see David's point about a plugin working upto a certain version of core (one example being the versions you have of Essential, where this would prevent users installing an older version on a newer core) - but I see two issues with that line of reasoning too:
1. (Minor) The plugins database already identifies what versions of core a particular plugin (or each downloadable version of that plugin) are suitable for - OK this proposal might work to prevent that user error, but seems like overkill the way it is presented at the moment.
2. (More significant) The main reason plugins become incompatible with core is because they are no longer developed. They are not designed and released to be compatible only upto a certain 'use by date' when they were published and if there is no one actively developing them, then there is no one to go back in and edit the version.php to add a 'best before'.
Perhaps Michael's suggestion of a min & max version for core requirements and identified dependencies would be a way to go - but the max version should probably be optional, or I can see developers just adding '9999999999' as the max version!
As I said - I can see Tim and David's viewpoint that my concerns were not the intended use case, or perceived to be a significant issue, but I still have that niggling feeling from a user/admin perspective, rather than a developer one, that it will lead to a level of expectations that are not intended by the proposal.