I see three questions here. My answer is not perfect, but I'll share what I've done.
You
You asked "How to avoid being seen as cash cow in my family"?
"How to avoid being seen as cash cow in my family..."
#StopStop lending to them, or, set strict conditions and follow through.
"..without being seen as a grasping and unhelpful person? "
This"..without being seen as a grasping and unhelpful person? " This is never going to happen. Your family has been trained to expect this and will be resentful of any change at all. They are wrong, but they willWILL resent you.
"My goal is to not give them any more money in the future."
This"My goal is to not give them any more money in the future."
This is a very good goal, and I approve of it.
"A thing I always ask myself is whether the problem I have is really on my own side and it should be okay for family members to ask for money even for non-critical stuff."
My analogy"A thing I always ask myself is whether the problem I have is really on my own side and it should be okay for family members to ask for money even for non-critical stuff." My answer to this is thealways The airplane air mask metaphor. Put yoursyours on first before helping anyone else. Your Your dream of owning your own home will not only provide you stability, but also enable you to help family in the rare cases when they are in actual need. You will be You are NOT helping your family in the long term by teachinghelping them to be responsible. If if you truly want to help them, you should help them learn to live on what they make.
Never give or lend anything you can't afford to gift, or any amount you will resent. EVER EVER!
If it is a loan, draw up a note with some amount of interest, a payment plan, and a real plan for conditions of non-payment.
When Friends and Family ask me for money, I always say "I see you are in need. The condition of borrowing money from me is that I get to ask all sorts of personal questions about your finances to see how you can get back on your feet". And then, I proceed to ask, how much they make, what they spend on, and try to come up with a plan that would allow them to pay for their expenses without me, or how they could actually pay me back. For instance: "I see you already paid for the airplane tickets, but can we call and cancel that nice hotel and book a cheaper one? That would get you x Euros towards dong this yourself. " Most people who are simply paying for fun things consider this way too much effort and go away(99.9%). The nice thing is, They can't really say you didn't want to help. And when they REALLY need it, they will be willing to go through this and you will ACTUALLY be helping them, and not enabling them to continue with a lifestyle they can't afford.
And then, I proceed to ask how much they make, what they spend on, and try to come up with a plan that would allow them to pay for their expenses without me, or how they could actually pay me back.
For instance:
"I see you already paid for the airplane tickets, but can we call and cancel that nice hotel and book a cheaper one? That would get you x Euros towards doing this yourself."
Most people who are irresponsible with their money will consider this process to be way too much effort and go away (99.9%). The nice thing is, they can't really say you didn't want to help.
And when they really need it, they will be willing to go through this and you will actually be helping them, not simply enabling their bad habits.
I've given about 3three loans under this plan. One One for school, and two to keep family members from being kicked out of their homes. I don't resent any of them, butthe three. But I don't get asked very often any more.