What Trump should have done is used his influence to get the GOP in Congress to fully repeal Obamacare in reconciliation and replace it with the free market principles that have been missing in the healthcare market for decades. Most importantly that would involve the repeal of McCarron-Ferguson and the phasing out of the tax deduction for employer-provided insurance.
The latter is only politically feasible when coupled with the proposed cuts in personal income taxes. And the proposed cuts in personal income taxes are only feasible with such a phaseout. That is because the healthcare tax break would effectively be replaced by the lower tax rates, and the lost tax revenue from the lower rates would be replaced by the phaseout of the employer health insurance tax break.
That was the clear and obvious combination to bundle and put into reconciliation this spring. And Trump didn’t do it.
Although I am prepared to cut President Trump a tremendous amount of slack (most of the time) because it seems virtually everyone is always against him, I think your comment at #58 is correct — Repeal was the proper first step, using the marketplace is the proper solution, and tying it all together with tax reform is the thing that makes it all work.
I’m not as optimistic as I was, but if Trump moves to tax reform and approaches this from that angle, he COULD still hit all those points, in a different order. I don’t know if he will try.