His Point #1: "we can buy drugs from canda". Wrong: it is illegal. It is soemtimwes tolerated (i.e. not enforced), and sometimes not. In the past year, for isntance, Google paid a $500 MILLION FINE for letting Canadian pharmacies advertize. Does this make it look like it is reasonable to count on buying from Canada? And It is reasonable to offer a solution to millions of people that is illegal?
His Point #2 is right.
His Point #3 is wrong - discussed above.
His Point #4 is, imho, only covering COBRA, which means that (a) people must have been covered by an employee health plan, and it's only good for 18 months. It does not apply to tens of millions of people (my guess is probably 100M US citizens, but someone my prove me wrong).
I have helped several people get insurance from such pools through volunteering in charity organizations. It varies by state, but, in the couple of states where I was exposed to it, the plans were horrible, with very high premiums, high deductibles, very poor benefits or all of them combined. And it is logical that they would be, since they group the highest risk customers. On top of that, you had to navigate a maze to be able to do it - which is why all these people at risk had to rely on volunteers like me to help them navigate it. This model did NOT work.
Sorry for the bit of passion here. I get hot under the collar when I see flagrant injustice and lack of charity for my fellow human being. And, btw, tomorrow this fellow human being could be me or you. Nobody should be forced to go without health insurance in this country.
EDIT: corrected my comments on point #4