I had no bennies of any kind at Garden World or the Florist in FHs I worked for. Those were my last jobs in NYC in the late 70s. St. Johns treated me as a charity patient when I ended up in their ER.
Where the COL comes in is - you choose to remain where the cost of living is so high you cannot afford the gap Ins. This is why I brought up the COL in my other post. If you lived where the COL is more moderate, more affordable and realistic, you could afford to pay for a good Supp. If I lived on L.I. RR and I probably couldn't afford a supp and probably a drug plan either.
This is why so many people I knew left NY when they retired. One guy I dated worked for the TA and got a good pension. He said even with their house paid off and his pension, they live much better in FL than they did in NY. Their retirement income goes so much further. Of course that money saved would cover their gap/drug plans.
Jerome was making plans the last I heard to leave College Point for FL and Pete was moving to the Carolinas once his house was sold on L.I.. My brother and his wife are now in FL.
My son knows if they stay in NYC they will most likely never be able to afford to retire. If they do, they too will be in your shoes where health coverage is concerned.