Yes, the health insurance one is the big issue in the US. Even with emergency funds after the COBRA period ends you simply cannot buy the same health plan individually, no matter what you were willing to pay. Many people are surprised by this.
Post-ACA there are plenty of good plans to purchase beyond COBRA so this is now really only an issue of affordability. They are rather expensive, especially for one who doesn't have a job and getting on Medicaid Expansion can take many months, if one is even eligible (which one is likely not to be if he's worked at all that year). Likewise, other ACA discount will not apply if one has made any decent amount of money that calendar year, I believe.
