troubleshooting Question

Eliminating Bad Email Addresses From a Marketing List

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jdanaFlag for United States of America asked on
Internet MarketingAntiSpamEmail Servers
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An friend of mine obtained a list of 10,000 email addresses from from a data-harvesting effort on an open-source state-sponsored website.  (My friends actions were covered by FOIA,  He then took 1000 of his 10,000 addresses and sent out a marketing email via MailChimp.  The marketing email was effective, but MailChimp complained that the 1000 addresses had a 16% bounce rate.

In an effort to weed-out the bad emails, my friend created a new Gmail account and built a .NET tool to send a test email to the 1000 addresses.  Presumably, any bounce in the Gmail account's inbox indicated that the address was bad.  

Initially, all went well. Bounces from bad email addresses and bad domain domains started appearing in the Gmail account's inbox, but then the following messages started to appear:

Technical details of permanent failure:
Message rejected.  See http://support.gTechnical details of permanent failure:
Message rejected.  See for more for more information.

The recipient domain wasn't bouncing the message, the GMail SMTP server was bouncing the message.  The bounce is understandable. Google doesn't want to be party to spammers.  One of its anti-spam algorithms picked up on my friend's .NET tool.  

My friend would like to minimize is impact the Gmail system and on the email recipients, but he would also like to weed-out the bad emails.  Suggestions?
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