The smart people at NPR Politics went through Trump’s “Contract with the America Voter,” i.e. his first 100 days plan, to see how feasible is.
For example, here is their analysis of Trump’s plan to gut the Affordable Care Act:

The GOP Congress has already demonstrated its willingness to repeal the insurance tax subsidies and Medicaid expansion portions of the Affordable Care Act, along with the requirement that all Americans have health insurance, using a fast-track legislative maneuver known as “reconciliation” that prevents a Democratic filibuster. President Obama vetoed that measure, but President-elect Trump would presumably sign it. The Congressional Budget Office predicts that could strip health insurance coverage from more than 20 million people – although the change would most likely be phased in over a couple of years. Trump’s replacement plan is less clear. Health savings accounts would allow more people to buy insurance with pre-tax dollars, and selling insurance across state lines might increase competition and reduce prices. But coverage will very likely remain out of reach for many. The requirement that insurance companies provide coverage to people with pre-existing conditions cannot be repealed through reconciliation. But preserving that requirement without the individual mandate to purchase insurance could create a costly situation in which people wait until they’re sick to buy coverage.

Trump’s rejection of Obamacare without presenting a true alternative for those insured by the program alone shows that his plan only creates a government of, by and for some people.