Graci -
I have to agree with Hope - he could be writing you letters, whether or not you send money, if he loves like he says he does.
I have 2 friends in jail right now - one is my best friend, and one is a kid who used to sell me crack, but always looked after me and tried to get me to stop the crack. My best friend is constantly asking me for money, even when I keep telling her I don't have it. The kid (who just started a 14-year-sentence) writes me every week, is TOTALLY supportive of my recovery and has really helped me a lot. He has NEVER asked me for anything. I try to send both of them a little money, when I have it and am comfortable with doing it. I sent money to the BF a couple of months ago, and will send a little to the kid today (along with a birthday card). All I ever hear from him is concern about ME, and he always says "I appreciate everything you do for me", even though all I usually do is send a letter.
When I get an "I need $$" letter from my BF, and I've already told her I am barely keeping my head above water, I just don't write back for a while. It took me a while to not feel guilty about it, but now I don't.
It's not always easy taking care of US, but I'm finding it helps me to not get dragged down into their consequences. I was locked up for 5-1/2 months, so I know what it feels like. It's not fun, but the necessities ARE provided for.
Keep taking care of you - you sound like you're well on your way.
Hugs and prayers!
Amy