I think you are fundamentally misunderstanding how and why Trump won the election - the key voting blocks that voted Trump and why. The independents and moderates among working/middle class in many of these swing states felt lied to and deceived by Obama's promise of change and hope. Obama didn't deliver in their eyes because things like wage growth were still bottomed out. It wasn't just white nationalism as is constantly mentioned for why Trump won. But those left behind by neo-liberal policies that had no trust for establishment Democrat standard bearers.
Michael Moore identified this important voting block early on:
This effect was borne out by
some data analysis after the election:
And now Trump's biggest advantage is really the economy. On paper its booming. And a lot of people are seeing gains. The message the Democrats really need to be focused on countering is that with that backdrop of key voting blocks that swung the election to Trump in mind
this should be troubling news:
So a lot of the short term benefits of the tax cuts and deregulation are flowing to some of these communities that felt ignored by the Clinton-Obama years while the long term problems won't be felt yet and even then more dispersed. If Democrats really want to combat the advantage the Republicans have gained in messaging they have to stop focusing on issues that won't inspire the independents, moderates and apathetic progressives and grow some courage on championing universal healthcare - their best winning issue for the next decade.