I am looking for suggestions on a software or an extension to work with Outlook, primarily to export emails with attachments (bulk exports of 50+ attachments).
Try Export Messages to PDF utility included in ReliefJet Essentials.
It's expensive, but our office uses PDFMaker, a plugin for Microsoft Outlook that comes with Adobe Acrobat Standard (~$300) and Adobe Acrobat Professional (~$600).
- Convert from one email, multiple emails (Ctrl+click or Shift+click to select multiple messages), or an entire folder at once.
- Convert to one combined PDF, one PDF per email, or a PDF Portfolio.
- Auto-archive files as PDFs.