To old users it might be somewhat obvious what time and day to ask questions. Not so much to some new users though.
Would it make sense to replay the questions that didn't get much of front-page views as much as others?
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What would you consider to be insufficiently viewed?
That aside, wouldn't doing that create a self-perpetuating cycle of replays since bumping older questions would get in the way of new questions getting front page time? (Especially on Stack Overflow where there's a steady stream of questions at all times.)
And in addition to that, people arrive at questions through various means - some look at the front page, some look at specific tags, some follow feeds, etc. Front page views aren't necessarily all that meaningful, although it probably depends on the site.
In other words, I think this request needs more research, details, and analysis of pros and cons.
If a question is asked during low-volume hours, doesn't that mean that there's less stuff coming in to push that question off the front page? It seems plausible that the questions that run the most risk of being lost are the ones that come in during the high-volume hours, when churn is greatest.
Also, Community♦ regularly bumps older unanswered questions, so we already have something to address the problem you're raising.