As it turned out, they were almost penniless (didn't have cash to timely file paperwork which was under $600 cost).

Wage slaves believe that accepting the system is the only alternative to dying penniless in the streets. 

I funded a deal, only later to find out they are penniless.  

Penniless I needed a place to live.

The tenants are penniless so if they break anything even if it's the tenants fault you are stuck paying for it because if it's not repaired Sec 8 won't pay you.

My dad died so penniless I had to pay to put his broker-than-broke a$$ in the ground.This was a man who could not get up again as soon as his good opinion of himself as suh-HE-ree-us was more than slightly injured.

Part of the deal here is was to give her the opportunity to find some place to move because she was penniless before the transaction went through.

., one of the world’s largest companies at that time; Leon Frazier, president of the Bank of International Settlements; Richard Whitney, president of the NewYork Stock Exchange; Arthur Cotton and Jesse Livermore, two of the biggest stock speculators; and Albert Fall, a member of President Harding’s cabinet.Twenty-five years later, nine of these titans ended their lives as follows: Schwab died penniless after living for five years on borrowed money.

The borrower is a penniless idiot that doesn't know anything.

What about a nasty divorce leaving one partner penniless when the scoundrel runs off with the savings and checking account money?