rules not working - done troubleshooting

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Outlook version
Outlook 2016 64 bit
Email Account
Long time user of Outlook and reader of in times of trouble / learning.

I'm trying to clean up and fix my wife's Outlook. In this long process I have:
  • cleaned out her inbox that had 2,000+ unread emails. Unsubcribed. Deleted. With what's left I created rules to sort needed emails, like friends' emails, into folders.
  • deleted all old rules
  • recreated the OST file. All emails and folders have repopulated.
  • recreated her contacts (from online cloud csv export)
  • created new rules. One rule is meant to sort her friends into a "friends" folders. I've tried this with all ~80 email IDs from her contacts.
    • One rule with these ~80 emails won't run automatically or manually.
    • I broke it into rules, each with 10 email IDs. Sometimes these seem to work -- but other rules do not work. They are entirely similar.
  • I've tried deleting a rule (with 7 email IDs) and recreating it. It will not work when run manually.
  • looking online for fixes -- I have renamed / refreshed her send/receive file (??) (link: Fix: While clicking reply all getting Not implemented error in Outlook — Tech Support )

Nothing here is working.
Her email account is an IMAP format with a major ISP provider.

Rules didn't used to be this hard. What's wrong?

Unrelated -- I use Sperry software Power Rules Manager to sort and clean up rules. There are now about 40 rules. (Some I hope to delete later such as after seeing that unsubscribe activity has actually worked.)

I am really stuck as to how to get these rules working!
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