I agree, while it may be codie of him to enable these situations, it's YOUR codependence that really speaks loudest in what you shared.
If you aren't married, isn't his money his to do with as he pleases? How is it your issue to control or manage? While I can understand being irked if he complains about a situation he's self-creating & how irritating it can be when we see someone consistently make the wrong choice - but it doesn't make it any less his right to make bad choices for himself if he wants to. It's messed up, but people self-sabotage in all sorts of ways.