Katie, I am so sorry and I know that kick in the stomach feeling when things go well...and then they don't.
My thoughts are that he lost everything the minute he picked up crack. He made the bad choice and knows where that leads, it's almost worse than the first time around when they didn't know how bad it would be.
It is entirely up to you to decide whether to charge him or not, but don't let guilt guide your decision. His bad behaviour (stealing) = his consequence (charges).
Whether you charge him or not, he's on a bad path that will probably end with jail anyway. Maybe next time it will be worse.
Doing the right thing is often the hardest choice...but it's still the right thing.
Hugs from my heart to yours.