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The two campaign-like stops will try and win over two different audiences that need to come onboard for Trump and Republicans to pass the the American Health Care Act - the bill that would repeal and replace the Affordable Care Act.
With strong opposition from both parties, think tanks, and industry groups, Trump's ability as a campaigner - and a salesman - will be on full display during his visits.
Nashville, Tennessee
The first stop on the "Trumpcare" tour comes in Nashville, Tennessee, on Wednesday.
The state is a perfect place for Trump to make his dual-pronged case that Obamacare is collapsing, and that his base should support the GOP's alternative.
For one thing, experiences in Tennessee highlight the increasing premium costs faced by some Americans under Obamacare. In 2017, the average benchmark silver plan offered on the individual health insurance exchanges in Tennessee increased by 63%, according to the Department of Health and Human Services.
Secondly, the decrease in choice that Trump and Republicans bring up so often is also an issue in the state. Four of the state's exchange regions have just one insurer offering plans.
Even Tennessee's state insurance commissioner Julie Mix McPeak said in August that the exchanges in the state are "very near collapse."
"I'm doing everything I can to prevent a situation where that turns to zero," she said at the time.
The statistics provide ample opportunity for Trump to hammer at the negatives of Obamacare, countering the rise in popularity for the ACA, which has been hitting its highest approval ratings ever in numerous polls.
Louisville, Kentucky
The other scheduled stop on Trump's tour will come Monday in Louisville, Kentucky.
This presents a different challenge for Trump, because the ACA was generally a positive for many Kentuckians. It forces the president to build a case for why the AHCA is a better alternative.
After the passage of the ACA, former Democratic Gov. Steve Beshear embraced the ACA by taking on both the Medicaid expansion offered by the ACA and creating the state-based individual health insurance market called Kynect.
Compared to the broader ACA, Kynect was relatively popular with those in Kentucky, and the percentage of the people without health insurance fell the most of any state between 2013 and 2016, declining from 20.4% of Kentuckians uninsured to 7.8%, a 12.6 percentage point fall.
The stats will force Trump to not only have to make the case for why the ACA is collapsing, but also why the AHCA would be better. This will prove more difficult, since analysis from the Congressional Budget Office and health policy experts have shown that support in the form of tax credits will decrease for recipients in Kentucky on average.
The visit is also about a single politician as well: Sen. Rand Paul, a fellow Republican. Paul has been one of the loudest critics of the AHCA and criticized the GOP's plans to repeal and replace Obamacare even before the introduction of the law.
The visit to Paul's home state will be a chance for Trump to push back on his criticism that the AHCA does not go far enough in its repeal of the ACA, and that there needs to be a bigger overhaul of the healthcare market. Trump even tweeted at Paul that the senator would "come along with the new and great healthcare program."