My Wife and I deal with similar issues every year. For the past several my Father in law is ALWAYS unemployed during the winter time. He either gets layed off or fired mysteriously in early fall. His basic plan is to work just enough through the year so he can claim unemployment and be off for an extended period. The unemployment obviously is never enough to pay the bills so they stack up until one day we get a frantic call just like we did 2 weeks ago that his gas is gonna be shut off in 2 days if we don't pay his $500 bill. Finally after 8 years of my Wife has finally had enough and refused to pay. For years I've told her money wasn't the problem it only enabled him to continue doing this to people. I also understand how hard it can be to say no to family in instances like this. However if you've helped in the past and they still continue to do the same dumb shit it's time to let them fall on the pavement.