So in Part I of the summer cleaning project, we focused on deleting the bottom portion of our closed question backlog: things that never got any love and just were dying a slow, cold death.
In part II, I'd like to address the elephants in the room: our once popular, yet nevertheless off-topic questions that are no longer a fit for the current Programmers.SE direction. Many of them are from the Ante-disciplining period, some are bad migrations from Stack Overflow, and we've accumulated others throughout the year.
Nevertheless, they're broken windows: they continue to attract pageviews and still show up in Google searches, compounding any quality problems we have.
Taking the closed questions with 20 or more up-votes, we have a total of 116 questions. Because of the number of up-votes, they will likely never attract enough delete votes from the community, and would have to be deleted by a moderator.
Before that happens, I'd like to see what everyone thinks: what should be done with them? Is deleting them now the best way to go? Are there certain questions worth saving, and if so, how can we improve them to fit the guidelines of the site?
This isn't official dictum: I'm asking personally about this specific issue.
This question, like the previous questions on the summer cleanup, are here to involve you guys in the process of what gets cleaned up. It's asked in the spirit of the community consensus that we should clean up the place, but that—as a community—we still need to work through the details of that cleanup.