no, i dont think you should send him any money, obviously you have a kind heart and he knows that. he has all the time in the world in there to work and if he chooses not to, thats his choice. but then he shouldnt be asking for handouts either. sometimes a person need to hit rock bottom for them to want to change and as long as you allow his life to be comfortable in there, then he probably wont change. of course theres nothing wrong with writing him and being there emotionally for him, but when he tells you he is going to do the right thing, tell him youve heard those words before so you won't believe him until his actions back up his words. this is only my opinion. I'll keep you in my prayers and i wish you all the best.