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If a person finishes working with Company A under H1B, they get 60 days 'grace period' to find a new employer. When they get a new job offer, they submit the visa transfer application, and receipt of the application by USCIS is enough for that person to start working at Company B. That visa transfer may take somewhere in the region of six months to complete, but the person can still work for Company B.

My question is: if this person finishes working with Company B AFTER the 60 days grace period is over, but BEFORE the visa transfer is complete, do they get a fresh 60 day grace period, or are they immediately out of status upon finishing with Company B?

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You remain in status for 60 days beyond the termination of employment. That's what the "grace period" means. When you are applying for a transfer along with an extension of status, that does not in itself give you status. Once 60 days after your termination from Company A ends, you do not have status. You can work for Company B by virtue of regulations that says you can work while an extension of status application is pending even if you don't have status, but that doesn't give you status. If you were to abandon the transfer and extension of status application, you don't get 60 more days of status, because you are not in status to begin with.

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