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[quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous]To clarify, the time share in Colorado is ours (we want it - though of course sometimes our children and extended family are sometimes invited) and we're "reclaiming" #2's condo in SF for us.

We're proud of #1 for pursuing a "noble" independent path, and of course we're happy to help him out when he needs it since he doesn't make that much money.  But the paradox is he resents us for "favoring" #2 but says he doesn't actually want that same treatment for himself.  Isn't that trying to have it both ways?

How can we "cut off" #2 without cutting off #1 though?[/quote]

Your real problem is that you think it's fine to permanently supplement your children's incomes. Please realize that this creates all sorts of unhealthy relationships and stunts the growth (in resilience and responsibility) of your children.

Apparently, choosing a noble career path "justifies" having a few perks from you. It shouldn't! 
DC1 isn't turning the help down, is he? So his job isn't all that noble, is it? He might not even have considered this path if you hadn't shown your willingness to fund a more luxurious life for him.
And then, DC1 feels guilty because his inactivity is somehow unworthy of receiving financial help??? That's ridiculous, because DC1 shouldn't be helped either.

My husband works in cancer research. He earns less than 6 figures with an MD and a PhD. He's saving future lives, and obviously isn't in it for the money. Our parents are not helping us, even though they could. We have enough to live on with our 2 children. Frugally. We prioritize education and culture. We are happy.

You have created a vicious cycle, and whatever you decide, it will be drama now or drama later. Pick your poison.[/quote]

OP here.  I don't expect Horatio Algers.  Nor do I think our children should be completely, 100% "cut off" or else be condemned as sinful ingrates by the likes of you.

We have no problem leaving aside some money for our children and grandchildren and help them from time to time.

Surely there's a middle ground here.

Take your 100% "tough love" attitude elsewhere.  I'm sure your husband has no shoes and ha to walk 5 miles to work every day in the snow, all in the name of "helping humanity" and not being dependent on anyone.  Nice platitudes, but it's not helpful here.  [/quote]

I must have hit a nerve, OP!

You're right, there can be a middle ground among reasonable people. But here nobody's reasonable, except perhaps your oldest son (who is sweet-talking but still accepts your money).
Your children have become used to depending on you because you created this dependency, so now the middle ground does not exist.

You should have a family meeting:
1. Announce a series of donations of receding value for the next ten years. At the end of this period, they will have to stand on their own. Telling them in advance how much to expect annually for the next ten years gives them the opportunity to create their own budget and make their own plans, and eases the transition from their present dependency to real adulthood. It is uplifting, not demeaning, for them.
2. Announce that your will benefits the grandchildren exclusively, not your children. That will incentivize their efforts to become financially secure within that span of 10 years.
3. Accept that "financially secure" will mean a working (or at best a lower middle class) income for your second son's family, when he and his wife get their act together. 
4. The real secret to life is that a reasonable amount of hardship and frustration makes you more resilient. You have to let your children take risks and live by their mistakes, otherwise this normal developmental process cannot happen, and they will always be weaklings, and will not be good role models for their children. Since you created the monster, it's your responsibility to try to make up for it... by helping them to become adults, not perpetuating the enabling.
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