The problem with the election in 2020 is that Trump already has a message and it is working in a large part of the right wing and independent voters: America First!
Such a simple message is absolutely what works in today's Twitter world. The tweet length messages are easy to respond to and force a gut feel response in voters. A feeling of support for those threatened by "foreigners" or whatever Trump has come up with. And a feel of hate for those that are the target (blacks, minorities) or those voters who support groups Trump and his folk absolutely hate.
I would not be too focused on what the voters can be given (healthcare, education, jobs etc) but go full force in some kind of TRUMP IS EVIL message. Never mind that Republicans are offended by coarse language. They will never vote for a Democrat anyway. Convey in simple terms that he is a hateful asshole.
If the Democrats are running a woman, I have to say that Hillary will be the one best equipped to challenge his every act and word. It will be easy for Trump to just label her "Loser Hillary." But she could just go full force on Trump supporters this time. Something like Trump weekly attacking "the Democrats":
But let’s focus more on Trump, less on his voters. The basket of deplorables. We Democrats may have some quite close by. If the candidate is another woman, I would get a male VP partner. The woman candidate can focus on the working classes that were ignored last time. They want simple things: jobs and healthcare. Do not offer them community college as a solution. You only have four years to help them. A raised minimum wage will work well. Their children can be offered the education. Then, with the caring candidate, you add a man VP candidate whose job is to go after Trump daily in the most clever and quick witted response and basically to be the attack dog.
I'll just offer a simple slogan: Vote for (Democrat), we care! Trump does not care about you.
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