Is it overstepping to sit down with her and help her figure out what is causing this major constant shortage?

It's tricky maybe, yes. But how much of this is borne of me not feeling comfortable to do so?

If you are thinking about it in those terms, Do it for selfish reasons, so you won't have to have the constant awkward avoidance all the time.

First, two things: 1. You have a good heart and are empathetic to the plight of others. 2. This is not your problem. Your two-ish questions: 1. I feel I am being more “middle-class” than I am being a caring person. You’re not. You clearly have class. You have already helped and this internal dilemma knocking at your conscience demonstrates you are a caring person. 2. I suspect I might be mistaken, or being overly “priveleged” about this because I can afford to prevaricate over principles vs hunger. It demonstrates you are very aware you cannot allow your compassion to be the solution to some strangers’ very difficult situation. Quite wise. Until your neighbours situation changes for the better, her request of your charitable offering is going to continue. All that being said, I think it is important to acknowledge your neighbour has paid you back in entirety. What to do? Do what you want to do! If you want to support the family by offering them 50 quid a month to see them through winter? Fine. It’s a good charitable offer. Be prepared that this is not going to stop after winter. But, if it’s only 50 quid, and you can get that fuzzy feeling of seeing the returns on your good will, well, that’s great. There most likely will be times when she will ask for more. Desperately. But you will not feel as bad saying you simply can’t that month. Or Don’t give her any more money. This is also fine. See section ‘First, two things’, sub section 2.

Another option if you feel comfortable: Instead of just giving her money, see if there is something she can help with: cleaning, laundry etc. This gives her a purpose and helps you out at the same time.

Blimey - tricky situation and huge credit to you for your kindness. I read the situation as that she does need the money and isn't wanting to take advantage of you as she does offer and has tried to return the spare money (albeit then needing it again). So that leads onto what the money is for. It could be that she is bad at managing money (which could be due to language issues etc). I'm think of something like she may have got herself stuck with an expensive phone contract to keep in touch with family/friends abroad or something like which is eating up large percentage of her income. Would be easy to get stuck with something like that as the devil is in the small print with contacts which is hard enough for a native english speaker to understand. It seems that someone like Citizens Advice service may be a useful place for her to go. They offer good advice and I'm sure will have experience of people in similar situations. If the money management is the issue and can be made more manageable then that will certainly help the lady (I'm making a lot of assumptions here of course!). After that hopefully money issues will become less frequent and you can both find something you are both comfortable with. https://www.citizensadvice.org.uk/

It is very kind of you to help. It is never bad to help someone if they are genuinely in need. Also rather than giving cash you can support her by buying groceries (That's what I do)

I think because there is a partner that hasn't completely left the picture, you need to be careful not to get in the middle even by the partner misunderstanding your kindness. First, protect yourself from misunderstandings or misperceptions. Second, how do you teach her to fish? The financial handouts might be okay short-term, but she needs long-term help. How can you best help her get to a place where she is meeting her own needs? If she might be struggling with communications, maybe the best thing to do, as someone else mentioned, is to guide her to the right resources. She needs financial advice, like how to create a budget, find ways to reduce her expenses and ways to increase her income. Long-term helping her to help herself is the best thing. Short-term, maybe pre-pay some bills for her to ease her financial burden while making sure the money isn't going to the wrong place like her former partner? Good luck with all of this and let us know how things go.

OK, so first off, you're a good egg sir. I recognize the internal struggle you're having, I've been there myself. A lot. Now, that said, I'm gonna be a touch harsh. Everything about this situation, to me, screams that there is a drug issue. I've seen it way too often. The abusive (but now returned) partner, the seeming constant (and escalating) need for cash. There's every possibility that any "support" you are sending is being spent on an addiction. Possibly for both her & the abusive partner. Here's the thing, it isn't on you to "fix this". IT IS NOT. Unless you truly, fully want to, and these things get very hard & dark very fast. Again, been there. It sucks. And often, you don't "win". Drugs are awful adversaries. I hope it isn't this, but the pattern is all too familiar. But here's what sucks. If it IS a drug habit, those kids are in danger. And if you report it to get the mother help, it could potentially mean the kids get taken away. Which... well, its not good. They're out of one shitty situation into slightly less shitty one. I've had to do this before. In the end the kids got taken away, the mom relapsed & overdosed, I lost track of the kids (the system basically told me to fuck completely off as I had no rights to know what happens to them). She was an old friend from high school. Anyway pal, I really feel for ya. Seriously. If you want to talk, just hit me up. Sometimes an ear can be a lifesaver.

There are may great viewpoints here, and really the first maybe hardest question is at what LEVEL do you want to be involved. I tend to want to be as far removed from the situation as possible, but just like with software to create a solution, you have to understand the problem. So far I would say the 2 options I have heard from the other responses is: 1. anonymize the donation (and maybe crowdsourced) 2. create a work-for-pay scenario, this is nice because it creates a tradable resource, which could be increased if there is a bigger need 3. 1 & 2 could be combined, but managed by you so that when need arises the fund is available 4. You could also provide this money in a gift card to a grocery store, which may slightly mitigate the ability to misuse the money This option seems the most equitable without spending too much time going down the rabbit hole. The further down, as @Mark Takata (Adobe) mentioned is VERY messy, relationships, bad decisions, drugs, etc. It’s horrible to admit but oftentimes kids are the last thing on the parents minds, and sometimes used as bargaining pieces. Where it goes from there is no easy solution, as shown by the returning abusive partner. Your desire to help is great, and noble. And it really shouldn’t be that hard to help out, but with anything boundaries are key, as the saying goes: if you give a mouse a cookie…

You have a good heart and I would lead with that. Often when one is in dire poverty, they are borrowing from Paul to pay Peter. They never get ahead of the game or have a chance to take a breath. I would look for a solution that would give her a chance to get ahead of the pattern. Perhaps offering to pay for her heating bill for the winter and setting up a monthly allowance at the local grocery store. Something like that might be enough to let her make decisions that turn out to be life changing.

Great suggestion, @Peter Amiri has a great point, the availability of money without the tools to use it wisely provide too much of an opportunity for it to be used for frivolous things.