Few years ago when I thought Hillary was going to easily win, I thought she was walking into a fucking disaster. At this point in her presidency she'd likely have one SC justice (I'm assuming Kennedy wouldn't retire) and that's about it on the achievement list. Lots of spending battles, no solutions on immigration, no ability to address Obamacare fixes, right wing violence/red states doing wild shit, Russian leaks of her admin's private documents, disillusioned young people/iberals/etc not showing up in future elections, etc.
If a dem wins in 2020 the same will likely apply. Gonna be ugly fellas.