You ARE brave and proactive...this is also therapeutic for you.
I know that anxiety from pushing him is stressful, but you will do this....do not *hope* that he is going to go...he is going, that is his ONLY option, you can state that clearly and calmly, it's your way or the highway.
i would also push the food stamp issue, the free cell phone issue and tell his father that you are taking action,.who knows, he may be in your corner after shirking responsibility too.
good thing you are on vacation but this is not fun.