I'm one of a close group of friends, we'll call them A, B, C, D, E and F. All of us are middle-aged. Of those, A (which is not me) is quite successful; he has his own home and family, a property portfolio, and has retired in late middle age.
The others have not done so well. Some have lost jobs. None have wives or descendent families. Some are living in inherited homes, some are trying to pay off mortgages alone and have little disposable income or space as a result.
Recently A has shown a number of signs of upset and frustration at the group. We've been trying to work out the issue but we're afraid that the problem might be that B's, C's, D's, E's and F's "failures" is impinging upon him. He can't have our kids over for playdates or leave his with us. We can't invite him to dinner parties or BBQs. Even if we just have a game night, he effectively has to host it; we don't insist that he does, but if he doesn't, he has to play on B's cramped table or sit on C's floor all while knowing that everyone's discomfort is because of his choice not to host.
Obviously, A is far too polite to directly say any of these, but A's other friends and wife are able to do all of those things with their groups of close friends. He's generally supportive, but equally showing growing frustration with the group when his filter drops. Some of the others are also depressed to various degrees as a result of the situation, and A is especially frustrated when they're affected by the consequent lack of energy in the group.
We can't easily directly talk to A because social protocol will require him to deny any upset. We can talk about it tactfully but we just can’t directly have A imply that this is what’s frustrating him, or imply it ourselves because that would make him sound entitled or accuse him of being such.
Obviously, we can't just choose to be better off, and as we can't talk directly, how can we approach letting him know that we want him to feel better and stick around, that we do feel grateful to him, and don't really want to lose a close friend over this because it would make everyone miserable, him included?