I have delt with this extensively, and personally pulled from further financial support of my mom. I basically took care of her for 3 years (took care of her and my dad when we as diagnosed with stage 4 cancer until 2 years after he passed) and for the last year and a half thought that I was more enabling then assisting, I kept trying to push her and encourage her to better her own situation but she wasnt trying to better her own situation at all, her only plan was basically(though I dont think intentionally) was to bleed me dry, I basically ended up wasting my entire savings trying to support her.
now every situation is different, but I think you should help if they: 1. recognize their mistake and what led up to the situation that they are in. and 2. are making their own efforts to better their situation.
my mom never wanted to recognize her mistakes nor make an effort better her situation.