If I read this letter correctly, LW has a brother that has successively drunk the most available saucers of milk dry in his (and his wife's) family of origin, and now LW is faced with being the last in her brother's food chain.

Personally, I think LW has already done everything possible, including establishing financial limits, attempting to provide advice and support and have gone so far as to establish trusts for their children that can help provide a "way out" if any of their children are self-motivated to escape their family of origin as they hit their teen years. (make sure those trusts are ironclad, and make sure you or someone you trust is the trustee and manages the disbursal...). The only thing you might do is to continue to pump money and support into his family in a way that benefits the kids, including clothing, etc.... but focus on them...... where the help can make a difference. If it works for you, invite the children to spend some of the summer with you, focus on their needs, send them to camp when their age is right - whatever is economically possible for you without going nuts.....

For LW, the challenge is a combination of survivor's guilt and a fear that LW has not yet done enough. In this situation, it appears that there will never be enough, and thus, measuring "progress" becomes a self-defeating end game. So, with an understanding that LW's brother is a bottomless pit of need, step back, adhere to the boundaries already established, and move forward with your own life. Finish that novel, seek a publisher, enjoy your life, and delight in raising your family. Take a look about how LW feels about her own relative success, and develop a self-awareness and self-respect about her survival skills, her resilience, and her ability to cope with the unruly vicissitudes of life.

The only other caveat is to maintain a sufficiently open relationship with the brother so that if there ever is even the scintilla of change, LW can capitalize on it.... The bro admits to a secret drug problem, for example, or recognizes that there are compelling issues behind his obesity and wants to know what to do about it (Overeaters Anonymous....) or he wants, finally, to clean up and get a real gig, and tenatively solicits advice on how to do that. In that case, the issue is leaving the ladder available for the bro to climb off his high horse......

LW may never know what motivates this sib to behave the way he does, there may be darkness locked up within his obese frame that will not bear the light of scrutiny. Until, however, he is willing to look at his own issues, all of the support in the world is simply palliative, and given his personality, will never be "right", "enough" or given "freely and lovingly enough".

Sending money across the country to parents of todddlers and expecting them to buy something is a bit presumptuous, especially given the nature of the relationship (were you close, actually, it would be easier to do that). Sending gift certificates, while more focused assumes that the brother and sister in law will actually dig them out and use them. Were LW to do that, a gift card for a major book vendor would cover off on the basis of giving. However, it is perfunctory at best, frankly, and one could never tell whether the gift card got used for books focusing ont he parents' needs or the kids.....

There are Crummy Trusts, set up with a specific focus on education. There are innumberable advantages, for you and ultimately for the kids. Even a few hundred bucks a year, carefully placed, will yield something when these kids hit college age. LW's brother and sister in law cannot hit the trust up, it is for the child... and LW can remain as trustee.

Is a 3-year old going to "get it"? Not at all, but they are also not going to "get" a gift of any sort from a faceless relative that lives across the country and plays no other role in their lives. The trust is dull, has no glamour under the Christmas tree, has no flashing lights or beeping sounds, but will, over time, accrue to something meaningful for these kids as they pursue either college or the school of cosmetology.......and in truth, the distance you have in relation to LW's kids precludes a more emotionally meaningful exchange. Moreover, given the straited relationship, contributing annually to the Crummy Trust requires only the most minimal of communications - a card will do. Then, when each kid hits 17, and their impecunious parents shrug their shoulders when it comes to educational planning, LW will have a modest nest egg that may take the edge off state tuition, a vocational program, whatever......and allow the kids to bootstrap out of their fiscal insanity.