You make a good point,Nino. One of my favorite scenes in the series was when Paulie had just scored a bunch of cash and we see him cutting out coupons from the newspaper.
I agree with most of your examples,but I don't know about Sil's hospital bill. Several times in the show Tony mentions that different peoples hospital bills will be covered by health insurance from one union or another.
Also Sil was a legitimate business owner(the Bing),so he may have bought some decent coverage since he could show legit income. If he croaked, then I would imagine he had enough life insurance(also legitimately bought)to pay the bill.
The only thing that could screw him up would be to linger in a coma for so long that the insurance would run out and he would wind up like Junior,except on a machine.

Unless of course Gabrielle figured to cut her losses and pull the plug.