Mind if I moan a bit? Maybe you can offer some advice. (Or consolation.)

My parents have been terrible with money. They are approaching 60 and have no savings. Several years ago they filed for bankruptcy. Some years after that, they had multiple credit cards (again) with lots of debt (again) and ended up in a debt counseling/repayment plan.
Besides this, my dad left a job a couple of years ago for one that pays about 25% less. As a result, with my mom's medical expenses, they only have about $150 left over after every month, and this would be IF they stayed 'on-budget' which they haven't been.
As a further result, when they have had a large expense, they have needed help. That help has come from my grandfather and from myself and my wife.
I believe strongly that we should help. Family. Honor your father and mother. All that. Believe me.
But at some point this has just become a drain. Money that we scrimp and save (and sell items, and work extra) for sometimes is just gone *poof* because they had some problem and we needed to help them.
I recently visited them (I live in a different state) and talked very frankly about this and their situation. My dad was open to talking about it (which was surprising) and my mom was in favor of it as well. We took a drive a listened to part of Dave Ramsey's audio-book (Total Money Makeover) [no, this is a not a DR topic, just so happens that a simple, straightfoward plan like his suits my parents very well] and then returned to the house.
Upon returning, we sat down and went over their expenses and created a budget (they did not have a written budget previously). Once we allocated income to all the various line items, they will be left with, as I mentioned $150 a month. I helped them open an online MMA and we put a little money in that. If they would accomplish the 'emergency fund' step I would be thrilled.
Anyway, the idea of this trip. The sharing of information. The sitting down and setting a budget. The savings account. The money saving ideas. All of that was designed to be a "teach them to fish" rather than "give them fish" sort of thing. I hope it becomes something worthwhile. I'd love to see them debt free except the house in a few years. They could do it, whether they will or not remains to be seen.
My question for the forum is, at what point do you help and what point do you stop or refuse? Since returning home from that trip, I've received a call from my mother. Some dental work she needed (and which I gave her $600 for, my grandfather having given her $900 previously) is going to cost an additional $700. When she told me this she told me that she had already sold some clothing on consignment for $100. She also said that she didn't want me to send any money. Bottom line though, if I don't, they can't come up with $600. I feel like the fact that they are trying to come up with the money on their own and trying to work a budget should be cause for 'helping' again. At the present time, I am considering sending $400 IF they come up with the other $200 first, by selling items or whatever.
This would accomplish a few things. It would help them. It would get them to help themselves. And it would keep them from being derailed from their budget which they have just begun.
However, I don't spend $400 or $100 or $50 on a whim. I do some work on the side to make even $50 every now and then for my own bills and debt reduction plan. This is why I said helping them is sometimes like a drain.
Anyway, what would you do? Anyone have a similar situation? Any suggestions?
Thanks.
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