Lending money to family

Hi everyone! This is kind of a personal topic, but I’m curious as to what everyone thinks.

My husband and I don’t make a lot of money. We’re lower middle class and have some savings in preparation for our baby, due in a few weeks.

Lately, his older brother (married with 2 kids and makes a lot more than us) has been asking for money. At first it was just $50 or $75 for “things that come up” but then today he asked for $300 because his water got shut off.

On one hand, he always pays us back, but it seems like a bad habit to get into, because what if one day he doesn’t and then it’s putting my family in a bad position? Emergencies are one thing, but unpaid utility bills are another right?

My husband feels strongly that we should help if we can, but $300 is a LOT of money for us, and my husband doesn’t want to ask if they’re having financial problems because my BIL acts like they’re very well off. I feel like it would be better if they asked for a little here and there and not a giant amount.

Thoughts?