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It is absolutely fine to reach out and gently ask for a correction, in my opinion. I have done it myself several times recently and all individuals contacted were quite happy to oblige me. The important thing is to be sincere and genuine in your message and remember that the person on the other end is likely busy so keep your message to the point and give precise instructions to minimise any need for back-and-forth email clarifications. Be patient - but chase after a month or so, if necessary - and do follow up to thank them for correcting once they have done so.

That's a tricky situation. I think you need to assess whether the duplicates are doing more harm than having no meta descriptions on the press release pages. Obviously the best solution would be to ensure unique content in the meta description - could content be extracted from the press release? The press release itself has presumably been reviewed and approved for distribution.

Your uploads directory is viewable. I would configure the hosting to disallow browsing directories.

Because WordPress creates a directory for each month you have two dozen pages being indexed by Google that show nothing but filenames ending with the .png extension. This is most likely where the keyword in Webmaster tools is coming from.