As someone who's dealt with mental health issues and had to be very informed on the subject, it's obvious to me that Robin deals with bipolar disorder(edit: just looked it up and he has indeed been diagnosed as such) and is either not taking his meds, or is on the wrong ones, and given his already strong presence, there's probably not a lot of people in his life, if any, who have the ability to "rein him in".
This is resulting in him making incredibly bad decisions, especially financially, which can only worsen his condition as the pressure and consequences mount. Robin likely needs to be in some sort of conservatorship before he totally ruins his own but also his family's life. It's a last resort sort of thing, but otherwise he will end up on the street or dead.
I truly hope he somehow gets on the right track again and gets the help he needs, but this is likely going to take some outside forces to intervene.