Can these 404 hurt my rankings organically?

Selected answers from the Dumb SEO Questions Facebook & G+ community.

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  Nes Tides: I have a large classifieds site that automatically expires content after a set period of days. This is more effective than relying on users to maintain their listings. I have a sitemap.xml that is automatically generated. I've noticed that sometimes there is a delay in Google Search Results not updating immediately (I realize I am just a small bit in the world Google indexes) and the page referenced goes to a custom 404 page I've built to direct them to a new search.
  
  Is this the optimal way to handle this scenario? Can these 404 hurt my rankings organically? Is there a better way to handle this in regards to SEO? Thanks in advance fro your help.
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  Suraj Gadage: +Nes Tides ;first of all for the pages that expires after a set period of days, you can use the meta tag "EXPIRES"to indicate to search engines when to delete page from their search index.
  
  Coming to the other question, instead of redirecting your users to custom 404 page, I would suggest to 301 redirect them to the relevant pages on the website to preserve search engine rankings and pass on link juice (if you have backlinks) and/or page authority.
  
  Hope this helps!
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  Nes Tides: This is perfect, the 301 redirect will do nicely! Thanks!
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  Jim Munro: From the expert panel in this week's SEO Questions hangout on air on 00:03:55 into the YouTube video: https://dumbseoquestions.com/q/can_these_404_hurt_my_rankings_organically +Nes Tides
  
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  Edwin Jonk: For reference take a look at this rather old blog article https://googleblog.blogspot.nl/2007/07/robots-exclusion-protocol-now-with-even.html
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  Nes Tides: It seems to me setting an expiration is counter-productive if you implement a auto 301 redirect solution? I realize that the 301 redirect will handle the 404 error while Google removes the content from search but wouldn't it be better to leave the expired element out there with a 301 redirect passing any rank from the expired classified to the 301 redirect destination for as long as Google keeps it in the index? Thoughts?
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  Suraj Gadage: +Nes Tides ;I agree. Auto 301 redirect should take care of the problem.