... He shops about 3 doctors to make sure he gets enough Ambien and anti-anxiety drugs. You think any of them pay him more then a moments attention? Anyway I know enough to worry and am pretty much powerless. Not a good position to be in.
Excessive use of these drugs may be part of the problem. Over time, they can erode our mental marbles, which we need for executive functions such as critical thinking, planning, etc.
Since you've been telling him for three years what he needs to hear and he isn't doing anything to fix it and is now approaching you for money, his addiction is in charge and is as dangerous to friends and loved ones as any other addiction. Addicts manipulate, wheedle, cry, cajole, beg, lie and worse - anything to put off the reckoning one more day.
I would not recommend your Iowa friend take him in until he hits bottom and gets professional help. The addiction would just turn your Iowa friend into another patsy to suck into its vortex of destruction. Any money you put in is just feeding the addiction so is worse than useless.
It's worth laying out the truth to him in tough language and telling him that you absolutely are there for moral support and to help him seek help, but not one dime of money. You've already lost your friend to the addiction, that's the only hope (though slim) to get him back.
Ah, speaking of Ambien, let me tell you a real story. It involves the husband of my wife's sister.
This man is in his early 80s, and had been taking Ambien for years, saying it helped his sleep. He developed an addiction, and went to many doctors to get it. He stashed the pills around the house, to be sure that he would always have some. He eventually lost all appetite, and did not care about anything else but his drug. First, he lost weight, then his mind.
Somehow, this eluded his wife's attention, until she noted his strange behavior. From a man who had OCD and germaphobia all his life, he changed into an unkempt addict, and acted like a lunatic. He refused food and drink, and nearly turned into a skeleton.
When his doctor sent him to a hospital, they had to put him in an ICU for a week. I don't know the full detail of how they helped him through the withdrawal, but after a month when he finally came out of it, he remembered nothing about this episode, or how he ended up in the hospital.
Some drugs have horrible side effects. Never take any drug lightly, particularly psychotic drugs.