We are a nation of Godwin’s Law (or at least some distorted version of it). Any time someone invokes an analogy to Nazi Germany, no matter how educated the person or how salient the similarities, we collectively and summarily dismiss the argument.
Bring up politics often and tactfully. Involve a diversity of opinions in your action group. Make a pact to engage with Trump supporters and report to each other about how the conversations go.
There is no good reason to think Republicans will pay a political price for repealing Obamacare.
There is no getting around the fact that a Trump vote was a moral failure. The explanations handed to us don’t survive critical analysis.