It sucks that healthcare is so expensive. I had a gap in healthcare coverage a few years ago when I switched full time employers. During that time I ended up getting a URI. I pissed around with it for a few weeks with inexpensive oral antibiotics, but in the end I landed in the ED with a fever of 101.9F and a right lower lobe infiltrate. I spent 4 days in the hospital and did a month of IV abx after that. During most of this time I wasn't able to work.
What I learned is that hospitals have slush funds for under insured people. If you really require treatment and are admitted they will assign a social worker to you and walk you through applying for state and hospital aid. Between the state and hospital funding it nearly covered my entire bill. What most people don't know is that hospitals can't render free care, they have to bill you and then help you pay (retarded, I know). So, what looks like an insurmountable cost is really manageable, esp when weighed against your health.
My advice, if he is not responding to oral abx, is to go ahead and get it over with (the hospital stay that is). If he waits he might well be off work for longer and in a worse off situation than he would be just taking a few days or a week and getting better.