Having spent more than a decade as a Shriner and a Mason I can speak to the subject of philanthropic endeavors...
We have several large causes which are well known
But we also have many smaller causes that are not so well known and many of those are established to benefit members, and their families...
We have found the following to be true...
those who need it the most, most times will not ask, mention, or allude to the need.
often the need is not met by efforts to help, this has caused 'multiple requests' for the same person.
The recipient is often looked at 'differently' by casual dona-tors (those who feel the need to help but may not know the person) things they do (go out to dinner, purchase what others perceive as non essentials, etc.)
recipients often feel undue pressure to make some sort of repayment (either time or money) which often adds to the stress of the situation.
those truly proud are often overcome with a sense of shame in the presents of "the group" this has led to members no longer attending functions.
these are all undesired effects caused by a honest attempt to help...
Charity is a strange thing...we ALL see the need and want to help, we understand that this is an unfortunate situation that is in NO way a reflection of the person in the situation, yet when we are on the receiving end of that it changes, it DOES (to us) reflect on us, it IS a statement of our "being"
Not saying this is a bad idea, just saying there is much more involved than just the who, how, and when this is a good plan...
Do what you can, if you can, when you can, pray you never need the same, and should you find you do...accept it as a gesture of love and respect, NOT pity, and be grateful that you have made such an impression of folks that they would do this thing for you!