I think I want to tell him to live on his own for a time and get his life together. I think I need to be without him for a time.
This sounds like a good plan. If he protests that he's going to do this or that for you - remind him he can still woo you from his own apartment if so inclined. (And you can decide, at that time, whether you're interested in dating him or not).
Also - beware any attempts to soothe you that are just to provide cover for him to raid the finances. Stand your ground about the financial stuff.
