Problem - not knowing when your searches will be archived / when they have been archived
Benefit - No surprises - if you're notified of an pending archive, you can make a choice about whether that is still relevant. If it is, you can then head into the search to ensure it is kept.
-Data and also any charts for that dashboard is lost upon archive and users aren't able to get them back - if this happens without knowledge this can be extremely irritating and time consumed to rebuild.
Problem - custom charts are wiped when a search is archived and do not return once restored so must be rebuilt or more often that not, would be abandoned.
Benefit - if charts are kept and restorable after archiving, you'd be saved hours of work on building charts and boolean.