Sure, but there's mechanism in real life that allows cancelling elections like sending your newly funded ICE goons to polling places. Ideally everyone follows the constitution but in reality (even looking at past administrations) there's nothing stopping the executive from taking an action and saying "oops guess we'll let the courts figure it out!"
I could see Trump trying this, but I also can see dozens of other people or groups, some richer, more powerful, more competent, and more ruthless than Trump, just waiting in the wings for the guardrails to come off to make a play to rule the territory of the former United States. If he tries and succeeds at this it's open-season. It's not a Trump dictatorship, it's a civil war, akin to the Chinese Civil War after the emperor fell or the Syrian civil war after the Arab Spring.
