Getting Prescription Drugs Paid For w/ Medicaid (any pharmacists out there?)

I’m helping a friend navigate Medicaid. He’s got Medicaid, with a, let’s say, $300 spend down. Let’s say his prescription pills for the month cost $100. Exacts aren’t important here. Since he needs to spend $300 each month before the Medicaid will pay any expenses, he never gets any relief on his drug costs, because he never meets the spend down. He really needed the Medicaid in order to pay for his pills, but cannot get any help with them.
I’ve investigated a few of the drug manufacturer’s assistance programs, but really just come up with dead ends, as in most of the programs offer the option to pay about the same as the local pharmacies with their discount plans.
I’m in Indiana. I’m not seeing anything from the state that says he has a right to his drugs. But, across the river in Kentucky, I see that a state website says that no pharmacist may refuse prescriptions to ANY person that cannot pay for their drugs, as well as minors, pregnant women, and a few other classes of people.
So my question is, would the Kentucky law apply to an Indiana resident filling scripts in Kentucky? I know there are a lot of one horse border towns in Kentucky so they come to Indiana to fill their scripts, so how does that work?
I’m thinking he should just transfer the scripts to a KY pharmacy and attempt to get them while pleading poverty. I think if I called a KY pharmacy, they would stonewall me if I directly asked, since they wouldn’t want to take on a patient that obviously wouldn’t payout.
A similar thing would be like the sign you when you go to an emergency room: They must provide services to pregnant women or anyone in need of emergency treatment, no matter your ability to pay. Surely an ER couldn’t ask about the patient’s residency, and say “You don’t live in this state, so the law doesn’t apply to you. Good luck.” So would it be the same for the pharmacy?
In another nice little twist, I told the pharmacy that my friend was on Medicaid, and I’d like his purchases reported even if Medicaid wouldn’t pay. They said that since he was using one of those discount cards, they couldn’t report the drug purchase to Medicaid, thus he couldn’t earn credit toward his spend down. A particular drug would cost $22 with the discount, and $49 if they reported the purchase. Is that really how things are supposed to work? Why wouldn’t Medicaid want you to use a discount card? It would delay you reaching the spend down, so would be in their best interests.