I like nice things. I often worked two jobs so I can afford nice things, with my own wallet. So I get it.

But he wants to have caviar and champagne on malt liquor budget and wants somebody else, a woman, to finance his life style. He is old enough to know that it’s not a noble thing to do. He is lucky he found two women to do it for him. Keep putting your foot down though. And maybe talk to financial advisor or a lawyer. If things go wrong, he’ll take half of your retirement investments/401k. You would take half of his but if he has none, then you are screwed. I’d start discussing his plans for old age. He has 20 years until SS age. Needs to start thinking

Please be mindful re financial situation. I know you are but when love blinds us we don’t always see things clearly. Just keep being strong

With his health there is not much you can do except encourage him to see a doctor. Health problems are not deal breakers for me if I knew about them ahead of time during dating and the person takes care of it or health problems unexpectedly developed during marriage and couldn’t be prevented.