I have to disagree with you Nino.

1) Tony - Hesh estimated his net worth at under $5 million (and he scoffed at this, as a boss should be richer). This was during his period of big gambling. By the end of the series it is reasonable to estimate that he has around $5 million put away. Even if it's just $3 million, that's plenty of money. Given that he was a boss, there were plenty of people kicking up to him that we never saw. Also, he never had expensive trials.

2) Jackie Sr - When asked if there was enough money after his death, Rosalie says "Sort of, not really". Which to me sounds like somebody who has enough money to get by but just wants more. Probably not rich but she was living and not working.

3) Silvio - He undoubtedly has health insurance. His wife will have enough of money to get by on without working.

4) Johnny Sac - He sent Tony to liquidate his portion of that Southern company that profited from the hurricane in Katrina (it was hundreds of thousands of dollars if I remember). Point being, he still had some money and owned parts of companies that the Feds and his own mob family did not know about. Ginny got to keep the house and her 401k, or something like that. She will not be rich but she will get by.

The rest of them I basically agree with you on.