I am in a similar situation as far as being better off than at least one, and arguably both of my parents. My mother is taking care of herself well enough. My father is in pretty rough shape, financially, due to a combination of bad luck and poor choices. Neither has ever asked me for money, nor have I offered (other than trying to pay back my mother for money she gave me for college, which she declined) or other support. Neither has compared my financial situation to theirs that I recall. In general I am not as generous as I could or perhaps should be, both to my relatives and to charities. I don't feel too bad about it most of the time.
Perhaps my initial cynicism in my response was because I am also in a similar situation and always have been, well at least since around college. My mother used to kind of ask me for things, get me to do things for her that ended up costing me money, etc. None of this was a lot of dollars, it was the principle. She'd do things like invite me to dinner then expect me to pay - because I had lots of money. Or ask me to stop and pick up a few things on the way over to see her, which I never got paid back for. It was never so blatant as to say "can I have $XXX."
At first I was too stupid to see what was going on. Then, when I caught on I just stopped. It seems kind of petty because it was not money I'd even miss, but then she'd start with little statements like you described - "Oh you guys are so lucky"...."You can afford to ..." that kind of thing. She's not very manipulative so it was just kind of subtle things that seemed to be to make me feel obligated. It may not have even been intentional. It could very well have been subconscious on her part.
I guess the similarity to the statement quoted is what set off alarm bells!
Then she won the lottery - I'm not kidding. It wasn't millions but it was many tens of thousands. At that point she had more money than my wife any I. I suggested she invest most of it. It was the mid 90s. If she'd done as I suggested she'd easily be a millionaire now. Instead I watched her systematically blow all of it over less than ten years. I knew when it was gone because she started asking for little favors again. But I simply ignored anything she said about that kind of thing.
She has long since learned not to even bring up money. She still makes comments about how we can afford anything we want. (Of course that might be true but only because our "wants" are modest.) Sometimes it is very hard to hold my tongue and not point out that she had an unbelievable opportunity when she won the money.
She is not destitute. She is married, gets social security now, and her husband has a pretty good pension as well as social security. So we are not talking about saving her from starvation. But there is no way I'd give her anything that wasn't a true emergency.
But unlike you Stannius, I think the experience has made me MORE generous. A large part of the reason my wife and I have so much is because we live well below our means and always have. We do both have high incomes, live in a low cost area, and have saved a lot over the years. We have way more than we will ever need.
So we do give quite a bit to what we consider worthy causes. But the criteria are fairly clear - we only give to "people" causes when we are helping people help themselves. We don't support any organization that just gives handouts to people. We look pretty closely at what the organization does before giving anything then we try to be generous and loyal with our support. We have similarly been generous to other family members in the past. But it's always a one-strike-and-you're-out situation.
And I don't feel guilty about any of it either!