I've done it.

I owed a $975 remainder on a $3000 e-room visit. I sent an email asking if they'd discuss a settlement and they just called me and said the debt would be written off completely.

I was going to open the negotiation at $900 because that's what I had left in my HSA account.

So clearly it pays to ask. In my case it probably also helped that I had already paid more than half the bill. But I didn't even have to plead poverty - I just said something along the lines of "I'm trying to figure out how to best deploy the funds I have, would you discuss a settlement"?

Yes people do this all the time, but YMMV. I could be wrong, but I believe the hospital is not obligated to work with you. Depends on who you talk to, the type of procedure it was, your household income and more. You're making $70k/year supporting a family of 4 in a tech-hub like the Bay Area, but say you had an accident vacationing in Texas and now on the hook for $8k in hospital bills. Will the hospital look at your cost of living or will they see 70k and assume you should pay in full?

Getting a $250k bill cut in half doesn't help so much when you used to make $40k/year before you lost your job because of the medical emergency.

One of the hospitals we had a child at had income based repayment and it was a sliding scale all the way up to 100-something thousand dollars per year of income. At the lower end of the scale, they cut your bill to a small fraction of the original bill.

I'm actually surprised this doesn't come up more in discussions about the cost of healthcare.

We were actually uninsured when we had our first child right around the time the ACA came into existence, and my wife had an epidural so it was about as expensive as a birth could be without a C-Section, and after the income based adjustment the bill went from something like $30,000 to only a couple thousand dollars I believe and they also offered a 12 month interest free payment plan.

It was definitely not a side of the industry that I had ever heard about.