The only position on healthcare that Trump has consistently taken is an overall lean toward single-payer.
However there is one specific thing that he keeps hammering home, and that is the absence of negotiation on the prices of prescription drugs, despite the US government being the largest single buyer (Medicare Part D).
"Who da hell would buy wholesale and pay retail?"
He knows it's because the drug companies and insurance companies have bought off the politicians, and has said so often on the campaign trail. Some politicians are "incompetent," but probably they're "taken care of" by the lobbyists.
If the federal government threatened to walk away from a certain supplier for charging too much, that company would lose access to nearly half of all dollars spent on healthcare in the US (i.e., what the government covers) -- a sector that accounts for nearly 20% of our GDP. We have their balls in a vice, and all we have to do is squeeze.
Trump knows that when Medicare Part D was signed into law by W. Bush in 2003, there was an explicit provision in it that there would be no negotiation of prices on prescription drugs. This was back when the Republicans still thought that championing corporate rape was a long-term winning strategy.
That law went into effect in 2006, and by 2007 the Democrats who barely controlled the House decided to push back in a follow-up bill that would have required the Secretary of HHS to negotiate drug prices.
It passed the House without a single Democrat defection, along with a couple dozen moderate Republicans. But most House Republicans decided that corporate rape was still the winning strategy, and voted against. When it reached the Senate, the only Dem defector was Harry Reid -- a harbinger of how disastrous Obamacare would turn out. And although 6 Republicans voted in favor, 41 of them did not, and it was killed by filibuster 55-42.
Of course, even if it did barely pass, Bush would have vetoed it and withstood an override challenge. So the Democrats were just posturing, trying to score populist points with voters, while assuring donors and lobbyists that there was ultimately nothing to worry about. That's how Obamacare played out, when they actually had the chance to make their wishes come true with a filibuster-proof supermajority in the Senate and one of their own in the White House.
Still, why did Congressional Republicans allow themselves to be branded as the party of corporate rape in healthcare? Out of sheer partisan polarization? Well congratulations, geniuses: if the other party knows that you're going to reflexively naysay any of their policies whatsoever, all they have to do is make an insincere gesture of populism, and without thinking you'll make yourselves the proud sworn enemies of the American people. Gee, how do we explain your abject pathetic failure in the next year's elections?
(Thankfully that shoe is now on the other foot. "Wouldn't it be great if we got along with Russia to fight Islamic terrorism?" IMPEACH THE KREMLIN-PUPPET TRAITOR!)
The utter failure -- indeed the fanatic insistence on not negotiating prices for something that you are by far the largest purchaser of, is so offensive to the common sense of a businessman like Trump, that he must have been howling for all of them to have been fired. The vote was reported by the media, so it's possible he heard about it ("I never forget").
Rather than be rewarded for populist gestures, the moderate Republicans have been slowly voted out, and only one of the Republican Senators who voted to negotiate drug prices is still there -- Susan Collins of Maine -- while many of the naysayers have easily held onto their seats. Same story in the House.
Fun fact: hardcore libertarian Ron Paul was one of the few Republicans in favor of negotiating prices. There may be a fault-line there to hammer on, where libertarian-leaning Republicans will have to prove their basic business sense.
Unfortunately, the list of "Republicans for corporate rape in healthcare" included those who would become major figures of the Trump era, other than the man himself -- Leader McConnell and AG Sessions from the Senate, and from the House, VP Pence, Speaker Ryan, Leader McCarthy, and worst of all HHS Secretary Price.
Since Trump has single-mindedly focused on negotiating prescription drug prices for Medicare, he has to know his point-man in the Cabinet has the wrong voting record on the issue. It's one of the first things he would've looked into.
It makes me think Trump is planning on digging up this corpse of a voting record and shaming the Congressional Republicans if they don't fall in line behind negotiating drug prices, if not yet full-on single-payer.
"What da hell kind of business sense do they teach you guys when you show up first day on Capitol Hill? ... Or maybe you were being taken care of by the drug companies' lobbyists? I dunno, folks, you think maybe that happened? Oh nooo, nooo, that never happens, especially not with the principled people in this room..."
If the majority of Congressional Republicans from 10 years ago were merely going against the idea out of partisan polarization, they can now safely go along with it since Trump is pushing it.
And since Nancy Pelosi, Chuck Schumer, et al. already voted for it then, they'll have to either go along with it again, or face a bloody revolution from their constituents, who want nothing more than universal healthcare. They would have to worry about far more than a tweetstorm from Trump -- he would camp out on their home turf, inflaming the rage of local liberals about how he's promising cheap drug prices and Pelosi and Schumer are getting in the way and going back on their voted promises from just 10 years ago.
He's got enough leverage over both sides to make it happen, although it would be easier to pass with a bare majority in the Senate. Ideally some other topic would force the nuclear option first -- no way McConnell would use it first for a populist cause.
Once he gets citizens used to the idea that we're going to use our collective bargaining potential to get killer deals and enjoy a higher standard of living, it'll soften them up to a gradual move toward single-payer. That could be his major issue for re-election -- "better than ever before" because we've never had a first-rate healthcare system like the other rich countries have for decades now.