You said: "Seriously? Regional airlines don't offer medical insurance?" Sometimes regional folks get talked down to by folks at the big boys and/or guys headed to the big boys (maybe that is or isn't you, as a military guy), and it gets old. Maybe that wasn't your intent. If not, I apologize. But even the lowest of the low offer some form of medical coverage. The "employer mandate" of the affordable care act says so. If you're dabbling in joining the 121 regional world, I assume you've visited "careers" sections of airline websites, and you'd see that our employers -- who have thousands of employees -- offer some form of health insurance, just as any other employer in America.