I have a cousin who we helped when she started divorcing her husband and needed to get out of their house with her son. She lived in our upstairs, and we occasionally babysat her son for her in the evening. Also, my dad helped fix her car, convinced her to change to a better lawyer, and is generally helpful. But she wouldn't get a job because receptionist jobs are boring and she won't work in a factory. And she can't work off hours because she has a toddler. The only person around who still gives her pity and attention is my mom, who always agrees that the world is just so unfair, she deserves better, yes you can complain all day I totally agree, no need to be proactive in any way.
So after all the help my DH and I, and my dad, give to her, I hear my cousin tell her mom that the only person willing to help her is her aunt (my mom). She said this while laying in my guest bedroom using my guest bathroom sharing our kitchen and living room with us and her toddler. For 4.5 months, before she moved to my parent's house because I wasn't having it anymore. After this experience, I might write the desperate family member one $500 check (at this stage in life, maybe more later), give them suggestions on jobs and housing, and see what they do. It's way too easy to be used, and we ended up in a situation where we were either putting up with her or kicking her and her toddler out, which I don't have the heart to do. I tried to explain our budget, and she said we were "rich" and "sharing the wealth" with her. So I at this point don't mind being vilified by her, and will hesitate to give the same amount of help in the future.