NEW (?) Window Previous Recipients Sync in Mac Mail?

i am about to sit down and manually transcribe my Mac Mail previous recipients into Contacts because there did not seem to be any way to get this into into Mac Mail under an individual group (I don't want hundreds of email address only contacts mixed up with my phone numbers but i DO want Mail on my iphone to be able to autocomplete with these addresses...) and i just want to check that there is not an easier way to do this than doing it manually.
i have three or four hundred of these so any help would be appreciated.
workarounds such as getting this data to GMAIL would be really great as well.
thanks!

And, some progress but more strangeness. After trying all else and deciding I might as well take the time to try the nuclear option, I opted for Rebuiding.  That worked, after a fashion, but not as expected:
The two messages which had originally appeared only on the iPad now also were present in Mail.app, unchanged in terms of content, time stamps, etc.
Of the two which had been only in Mail.app on the iMac, one disappeared but was discovered in Deleted Messages. The other one was still in the Inbox, but a new timestamp, about 8 or so hours earlier than the one originally showing, caused it to be displayed much further down in the list.
A Mail guru might be able to divine some clues from the above. I've noticed occasional and brief disconnects between the two platforms before, but nothing this obvious or with this duration

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