This last piece is a little disingenuous.
It's VERY hard to negotiate a plan for a small campaign. He's probably just scaled up enough to even negotiate it (about 50 is the break point). That's less on mayor Pete and more on our ridiculous, counter intuitive and irritating for profit health care system. Also: the exchange is a hellscape and all of that "consumer choice" doesn't matter at all when you have to navigate it. Speaking from experience here.
Also, i've never worked on a campaign on the scale of a Presidential campaign but even being paid staff AT ALL is kind of crazy huge. Most people are volunteers, even if they put in 40-60 hours. That's just how our system works.