If your visa is still valid for entry you do not need a re-entry permit.
If you do not want to deal with the medical insurance requirements you could leave without a re-entry permit needed to keep you current stay valid and then re-enter the country after your visa expires and get a 30 day visa exempt entry. You could then apply for a non-o visa at immigration and then a one year extension based upon retirement.
The $10,000 covid 19 insurance is only needed for entry to the country. You would only need 30 days of coverage if you entered visa exempt.