I am going to disagree on this one. Tony was not broke and we only see a small portion of his family (they only really show the membership of two crews). Rosalie Aprile seemed to live very comfortably for the entire series run (France trip and that house come to mind). Junior only became broke because through his Alzheimer's he likely forgot where the lion's share of his savings was. Paulie clipped coupons and extorted old ladies because he was a frugal shortsided petty crook. That was part of the humor in his character. No where is it ever indicated that Sil is a brokester. Vito left with a duffel of cash and there is no way of knowing whether that was all he had or not, but his widow continues living in that house. Carlo, Patsy, and the other Capos ONE TIME had to be lectured about their lack of production (Something any decent sales manager or small business owner will tell his middle management from time to time). Johnny Sack did to an extent go broke. While the feds seized many assets including his Maserati and vintage Wurlitzer (lol), there is no indication that his wife was destitute (other than her having to work a part time job to help out). Puss did leave Angie with very little, until she got off her lazy ass and took the reigns of the small business he left her.

The ranches, two story, and split level houses that DiMeo family members are seen living in did not look like pieces of shit to me, just middle class American homes.