I guess you have to decide for yourself if you accept his help and get your act together or keep hanging with bff and wind up in jail again or dead, etc. If you get a job and apartment and things are better when she gets out of jail, then what? She will have no job and will be pulling you away from yours and down you both will go again. What do you want? I would stick with whoever was going to help me get moving in that direction and/or worry about the relationships when I was more stable.