I've been in the situation where I realised that I wasn't helping by "being kind".
I had a friend whose life fell apart through no fault of her own and suddenly she went form being fine to struggling. Like you, I couldn't bear to think of her children being without, so when she popped round and said could she borrow money to get new shoes/food/cereal etc I always gave it.
And she paid me back at the end of the month.
But each month she owed more and more by the end.
Because at the beginning I gave £25 for shoes, and she bought shoes.
But then she started asking for £25 for shoes then appearing the next day saying they'd gone to buy shoes but seen a DVD of something they really wanted to see, then had ordered pizza because it was a treat night and they'd had a lovely night but now they still needed those shoes.
It got to the point she would owe me £200-300 at the end of each month, which we didn't really have spare, and she didn't get that much in pay so she was starting each month money down. I then realised that by just freely giving, I was enabling her to make "bad choices" because she knew she could come back and ask again so she didn't have any worry about spending more - but then she'd have less money the next month.
She was always going to be rich in the next 6 months in her mind!
So I started not having money always. So if she popped round for £5 for cereal then I didn't have the money but she could take a box. Or £25 for shoes and I'd have only £22 in my purse.... just to make it clear she couldn't come back the next day.
When she moved away I discovered she'd been doing the same to at least 3 other people, so when I thought she was owing £200-£300, it was closer to £1000-£1500 at the end of each month, so she was starting each month in debt. One of the others she rarely paid back too - when she left she owed him around £2k.
Now the issue was that she was struggling, but she had no ability to say "no" to herself in the face of something she wanted because there was no accountability. When I started tightening up, then she did start being more sensible. And at times the money she owed me, a good half had gone on treats that I wouldn't have spent money on (like ordering pizza in) because we couldn't afford it.
I realised that in "being kind" I'd enabled her to get into more debt and put her in the situation that was ultimately worse for her.