The conditions that allow someone like Trump to come to power are manifested by the neoliberal policies extolled by the Democrat and Republican establishment, alike. Your party leaders are Reaganites/Thatcherites. The biggest policy win for Democrats in recent history was a Heritage Foundation plan that acts as a de facto subsidy to private health insurance.

And most people do not live in swing states so most “protest votes” do nothing to tip the scales.

creating more division within the left

Liberalism isn’t the left.

create more Republicans in the process

Create more leftists, actually.

ivory tower orthodoxy

It’s the Democratic establishment that abhors populism and typically walks in ivory tower circles. Liberalism and neoliberalism are the dominant ideologies in the Ivy League schools, not socialism.