I wonder what their response would be if you said yes you have US health care insurance and are coordinating their signature on their Health Certificate?
As the new rule does state "all foreigners apply for a one-year permit to stay on an O-A visa" does lend interpretation to require it for Retirees applying for a one-year extension.
The reporting is suppose to be done within 24-hours post returning and it’s the responsibility of the “house master” to report but if they don’t you will be held-up from renewing your extension.
AJ Martin - great touring if you’ve never been there, to include: Sentosa, hawker food, Music in the Park (also a good running route), Little & Big India, Singapore Night Zoo Safari, Merlin, Clarke Quay (nice waterside resturant area),...