Giving the gift of debt

Tim's mom called us the other day to check in, and to wish him a happy birthday. (Four days and counting, for those of you watching your calendars.) She also informed him that she was dropping $100 into the account for the combination of Tim's birthday and our Christmas presents.
Tim's mom tends to give cash because she figures we can best decide what we want. In addition, it means she doesn't have to go out shopping. With her congestive heart failure, surgically repaired knees and bad hip, Nadine has trouble walking any real distance.
We definitely appreciate the influx of cash. Tim will take his $50 from the birthday money and probably buy himself a video game. Our combined Christmas money will probably go to cover any gap between our Swagbucks and the cost of the iPod Touch.
Still, as nice as it is to get money, I always feel weird taking gifts from Nadine. As I've mentioned before, Tim's parents are not in a good financial situation. They have exactly $0 in retirement funds. His mom is on disability and gets around $1,100 a month. But she won't get Medicare until this summer. Meanwhile, his dad is unemployed. So they are living on under $3,000 a month (and just their space rent is $500, who knows how much the mortgage is). They still owe money to the IRS, too, and some undisclosed amount to a credit card.
I think my hesitation is pretty understandable. I was raised to be frugal and careful with money. More to the point, I was raised to discourage gifts that I didn't think the person could afford. At the very least, to make it clear I wasn't asking for/expecting anything.
There are at least a couple of bloggers who have weighed in on this subject. One had a relative who, despite massive amounts of debt, always spends lavishly on gifts. She had mixed feelings about it.
Tim, on the other hand, has no qualms with accepting the money. He figures if someone wants to give us something, it's silly to turn it down. I'm sure it helps that his parents spend so much of their time, energy and money on his brother, Matt. I think Tim sees gifts as their chance to show him that they're willing to spend money on him, too. In addition, Tim's pretty sure that if they don't spend it on him, it will end up going to Matt one way or another.
I guess I understand this outlook. But it's hard for me to shut the guilt complex off. I just keep thinking of how much more Nadine probably needs this money. We're not doing well and, yeah, we have a lot of debt. But we have things to fall back on. She doesn't. She has to make the $1,100 last all month, while still paying some household bills and any of her own medical costs.
In the end, I suppose, it comes down to the usual lessons I have to learn:
- I have far too much guilt and should just let things go sometimes.
- I can't control other people or how they spend their money.
- Just because they aren't the choices I would make, doesn't mean they are wrong.
- It probably makes her happy to be able to give us something.
So once again I will probably be taking a cue from Tim and just enjoying the moment. I will thank her graciously and will be sure to tell her what the money ends up buying. That way, she can know just how helpful her gift was.
Do you have any similar situations in your own life? How do (or would) you handle them?