--SNIP-- Second: Old version of Wine are still quite used because of package managers just offers "stable" Wine versions over the "unstable" ones so I would like to see another popup or warning in winecfg that informs user that their Wine is getting old... so after specific number of days(from release of Wine version X) counter gives some warnings about old Wine version.
Having a popup (or anything that requires user interaction) could get really irritating - there are situations where people would use an older version of wine on purpose. Like if a large organization uses it to run one specific app, and has a specific version that works perfectly, they might not have any reason to update.
How about a fixme when wine is run, informing them that the version they are running was released X long ago, and that if they have any issues they should try a newer version?
It'd be nice, too, if people then reported bugs with that on the top of the output - it could save a lot of work chasing down already-fixed issues.
--Matt