I feel that it was "too much" by the third time. We all make mistakes, once, maybe twice, but at three times you have become the enabler.
You need to put your foot down, not tomorrow but today. By bailing him out each time you are enabling this destructive behavior.
Please consider my answers here as I have a 21 year old son, a 19 year old son, a 13 year old daughter, and a 5 year old son.

Originally Posted by
fearlesspink
Everytime we have gotten him out of what ever trouble he has gotten into.
See, he KNOWS you will "bail" him out. He is not responsible for the consequences to his actions.

Originally Posted by
fearlesspink
He will only work 30 hours a week or he "gets sick"
Again, he knows you will bail him out. You have to stop enabling him and make him pay for his own actions. Yes, it is hard, but MUST be done if you want him to be responsible.

Originally Posted by
fearlesspink
We are feed up but what do we do?
Make HIM pay, he did the "crime" so to speak, he must do the "time" again so to speak.

Originally Posted by
fearlesspink
He can't afford to live on his own
He could if he had to.

Originally Posted by
fearlesspink
if we make him leave how will he make it
He will have to buck up and work 40 hours or get a second job. He will do this if he HAS to.

Originally Posted by
fearlesspink
and how do we live with the guilt?
You won't feel the guilt once he has learned responsibility, and it may be a bitter pill for him to swallow, but he will, eventually.

Originally Posted by
fearlesspink
you know we are attempting to make him pay back all the he owes us due to the above mentioned and are worried if he moves out he will never pay us back!
This will probably never happen. So it is best to cut your losses and start with a clean slate.
You see, as I said above, you are enabling his destructive behavior. Not only is it destructive to him, but to your marriage as well.
This is something we all as parents have gone through in one way, shape or form in our lives of rearing children.
If you don't nip this in the bud now, where do you think he will be when he is 29 or even 39? Still at home with Mom and Dad taking all of the responsibility for his actions.
It is time you bite the bullet, lay down the law, and MAKE him suffer HIS consequences. You have done your share of suffering. He is now and adult and, as such, needs to learn to be one. Even if you have to use tough love to get the point across.