Man, that’s a tough timeline to read through. 

I don’t think you could’ve done anything more to help this guy out or try to set him up for success. 

The way it all ended kind of sheds light on the quality of individual he is though. 

Internal chaos usually is reflected by external chaos.  If your internal life is out of control, your outward life typically depicts that as well. 

Hopefully he’ll start to see things more clearly and put some work into growing and changing towards a higher version of himself soon.