RevivingOphelia.....OH, girl.....you are in the same situation that millions of loved ones face, with family members..... I have faced it, also...
It is so easy to tell someone else...just say "NO". And, maybe that is the answer....
I want to say that I get where the really difficult part is-----Most of us were raised, being taught various moral values....in our family, in school, in church, or the culture, at large.....WE are taught to honor family--to always be there for out sister or brother--that it is good to be charitable--"there, but for the grace of God, goes me", blood is thicker than water, family must always stick together, etc....
We are NOT, usually, taught what to do when a struggling person is not pulling their own weight as much as they are able....or when they are taking advantage of circumstances...or, defaulting on their own responsibilities....and when they manipulate us by tapping o n our own good nature....
This causes us extreme inner discomfort and lots of guilt feelings when we are implored to act against what we were taught.....it feels like a "twisting", inside...
And, it causes a jumble of emotions...sadness, anger, confusion....
Here is my own personal take on it....I think it is o.k. to write the letter, if you want to. Now, I doubt that it will change him, and, probably not make any difference in his future behaviors....not, based on one letter by you....
But, if it makes YOU feel better...then I say to go for it....(if he is entitles to ask--you are entitled to have your say!)......
We all have to live with ourselves. Myself--there have been times that I have sent the money...and, times that I have said "no". I guess it all boiled down to circumstances and how I was feeling at the time.....
I do think it is good to remember that asking family is usually the easiest way out...especially, when the "problem" is drugs and alcohol (only).
Human resourcefulness dictates that they will find another way to get what they need/want, if the family doesn't come across,first.....
You sound l ike a very caring sister, to me. I can see that you are trying to do the right thing..... my heart goes out to you....
I just offer my thoughts on this in the hope that they may be of some help to you......