These situations take two-the freeloader and parent who grumbles, but happily writes another check.
This is what I think as well, but I do understand why some parents do it. My father, for example, lost his mother to cancer when he was only 24. His dad left the family when he was little, but has somewhat reentered our lives. Believe it or not, my dad is a powerful, influential member of our community and has done extremely well for himself and his family (including me) with his business.
However -- my brother has found his weakness (a desire for strong parent-child relationship) and takes complete advantage of my dad!!!!
My parents told us that they would help take care of us as long as we were in school pursuing a degree (a very generous offer), so my brother has been in & out of college(s) for 7 years and still does not even have enough credits to be considered a sophomore. Yet, every time my dad says he's going to cut him off, my brother starts threatening to kill himself. I have my Master's in counseling & am aware of his behavior & (just like my dad), I fear that if my parents actually went through with cutting him off, my brother would actually go through with suicide - just to get back at my dad.
I have tried to get him in with the best counselors in the area (I'm in school counseling, not mental health counseling), but if a client does not want help, it is often difficult to give it to them. Medication also doesn't work with him. He has tried nearly everything, but the only results seem to be an addiction to xanax.
Fortunately, my dad can afford it, but my parents are devestated. My mom is embarrassed to talk about my brother with anyone but me, so I often feel upset & angry too. My mother says that when the phone rings & his number comes up on the caller id, she gets sick to her stomach. They do love him, but my parents claim that if it weren't for me & my children (& DH), they would lose their minds.
It's that sense of "entitlement" that controls my brother & others like him. He knows how his behavior affects people, but he really doesn't care. He wants to enjoy the "good life", but he doesn't want to work for it.
I could go on & on (& on & on) about my brother's behavior, but I won't waste anymore of your time. I deeply sympathize with anyone who has to deal with someone like this.