Gosh, a lot of people here don't like to help relatives.
The advice that's been given here certainly comes across as uncaring at times. But with all due respect, I don't agree with this interpretation. I believe that people here are warning Tomcat to run away because they HAVE wanted to help their relatives, have done their LEVEL BEST to do so in many cases, and have experienced a painful and negative result.
It's not just a question of WANTING to help, it's a question of whether you CAN help or not.
Logically, you'd like to think that everyone is a responsible adult. But many make decisions as though they are still children.
You'd like to think that they'll welcome help from relatives and friends and be grateful, or at least neutral, about the contribution. But many of them resent the help and blame the kindhearted volunteer for ruining their lives when things don't go well.
You'd like to think that they'd be delighted when their loved ones make good, especially when success was won by dint of hard work and LBYM. But many are jealous and angry. When others do well while they do poorly, they feel "less than" and they lash out in response. Any advice you give only reminds them that they're losers in comparison.
I think this pretty well sums it up:
Over the years my parent has tried to help her but I think it has made it worse. ... I am also a little concerned that everyone has their hand out when this occurs.
It's my experience and the experience of many on this board, from what I can tell, that helping people causes them to want and need even more help. Bailing them out leads them to believe that there will always be a soft place to fall, and that they can continue their immature ways. Lack of negative consequences is no favor to them. It is, in fact, a penalty. Providing them with someone to blame (yourself) only delays the time when they step up and take responsibility for their own decisions.
This is absolutely heartbreaking, when you're talking about someone you love. Standing by and watching your Aunt fritter away the only lump sum she'll ever have, without trying to save her from herself, will be difficult and painful. But realizing that you CANNOT help, and can only make it worse if you try, may help you to get through it.
Alternatively, you can realize that you're going to take it in the teeth whatever you do, and get right with her lack of gratitude and blaming behavior before it happens. If you expect nothing out of your effort, but only make it because it's "the right thing to do" in your boook, then perhaps you can minimize your inevitable frustration and hurt.
Given your feelings for this person there is probably no easy way out. Such is the human condition, alas.
I wish the very best of luck to you, whatever you choose to do.