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It sounds that he had been enabled for quite some time through the financial assistance.
It is time for him to stop relying and taking advantage of you. He is an adult and generally individuals start to learn about work and independence and earning money earlier in life.
Advise him that you will not be able to continue supporting him. Let him know that you would be there in crisis and to provide encouragement but it is really time for him to start being proactive.
If you continue in the same way, he will not have the motivation or reason to change his behaviors.
Have him go out and apply for jobs, go to the dep of labor for assistance, whatever it takes. Let him know he will need to cover his own phone expences etc.
1)You can help with the health fees for him. That is understandable. Individuals who are depressed tend to socially isolate, lose interest in activities, etc. Social interaction and having a structured day such as at a job setting may be good for him. He could look for minimum stress jobs like at at book store, or something low key. So, you letting him know you would have to stop with some of the monetary support in order to let him earn some money for himself and feel good about being self sufficient won't necessarily send him into crisis. That of course would depend on his coping skills and true desire to work on himself and the situation. If you let him know that you would only cover the essential fees until he finds a job is not sending mixed messages because you would still cut off the other minor bills.
2)You could give him few months (it is hard to find work) but he can at least seek PT jobs. Some part time jobs like Starbucks pay health benefits to their employees.
3)You may want to allocate some time to specifically go over this with him and to make sure he knows you meant it and will be following up with this.
4) the dept of labor provides job/resume services/training and you would want to make sure he signs up for this and goes to it
5) he can also try to look for on line jobs at the rat race rebellion website. Having few little jobs making some money is better than being jobless.