That $300 per month you're paying for the whole family - does it include employer's contribution?
From my experience, a decent insurance for the family is somewhere in $20k-ish range per year, which is closer to 10% of your income.
This lines up with 10% UK National Health Services charges HM's subjects.
It will not have a similar level of quality though, forget it. The lines will get longer and the definition of "medically necessary" will become way more frugal.
And for your income level it probably won't cost you less. Neither for mine. Nor for that of many HN users. But it will solve SO MANY annoying problems for so many people at once that I still think it's justified.
First, losing job does will not mean you're losing your medical coverage. You probably have not lost a job for a prolonged period of time. Neither did I. But the fact that it might potentially happen gives me uneasy feeling. If (when?) I lose my job, medical insurance will be the single biggest charge on my account, probably more than all other stuff combined.
Second, all these infamous cases when someone with insurance was admitted into the hospital, but then it suddenly turned out some junior aide to the senior anesthesiologist is out of network, therefore the insurance won't pay him. This doesn't happen often enough for most people to start pestering their congressmen, but it nevertheless happens.
Third, it will make the gap between salaried employees and contractors smaller. There are a lot of talks about whether such-and-such is actually not a contractor, but a salaried employee. And usually it all drills down to the benefits the person receives. One of the ways of solving this problem is making the benefits the same for contractors and for the employees. While it will not close the gap completely, it will make it more palatable.
Fourth, those willing to get a higher level of service will be able to buy private insurance. In countries with national healthcare private medical insurance is cheap - may be 10% of what we're paying now.
I can keep going. The trick is that none of these cases on its own is big enough to affect the majority of population, but combined I'm sure each of us will eventually be hit by one of them.