There was an interesting Question and Answer on Slate the other day about helping family members who perhaps aren't as financially stable. The asker is doing well, financially speaking, but some of her siblings are not, and some really struggle. She wanted to know how she should best help them out - according to their needs or everyone getting an equal amount.
First off, the key here is that the asker wants to help her family, she doesn't feel obligated. It's an iffy situation as to whether or not there's any sort of obligation to help family in dire financial straits. I think it really depends on the situation, but here, she feels no obligation.
I like the answer. If you want to give money to family but aren't sure how best to distribute, freedom from want of necessities should be the priority. Make sure people have food and shelter. After that, it's up to you.
Family and money are very hard. My parents have always been all about fairness. When I was moving to D.C., my brother was in the process of buying a house, and my parents were helping him out with loans (which he has already paid back) and a small gift. I thought this was great, and so nice of them, and never worried about the fact that he was getting something I wasn't. When my move was complete, my parents handed me a check equal to what they had given him, because that made it fair, and they knew that I had some big expenses with the move. It was incredibly nice of them, but definitely unnecessary. They just didn't want to create any animosity (plus I think they liked that they could help me out a bit too).
Loaning money to family is always questionable, just because of the difficulties it can cause, so if possible, it's always best if those loans are treated as gifts, or at least thought of as gifts (and then you can be happily surprised when your family member pays you back). And gifts can cause animosity between those receiving gifts and those not receiving gifts. But I would like to think that when a family member is struggling to buy food and another family member very kindly gifts them some money for groceries, that a third family member wouldn't sulk because they didn't get anything. But you just never know.