Theoretically, Obama's plan is brilliant.
He intends to destroy as much of the system as he can, in order to force the country to come back stronger. Like burning down a house to fix a leaky roof, because the wife maxed out the credit card.
If I was really selfish, I would support single payer, because by the time it's enacted, I'll be one of the retired people mooching off the work of the healthy young'uns. Trump just wants to make us earn that retirement.