Which election was more difficult to win?
2016 based on the fundamentals was more difficult to win for the Democrats. On the other hand, Bush was a more formidable opponent than Trump. I guess 2016 would be my answer as I do believe Hillary would've lost to a more polished, competent opponent, and that's even if she ran a better campaign than she did against Trump, whereas I think Gore would've beaten Bush with a better campaign and would've beaten any other Republican that ran that year not named John McCain by a decent margin, good campaign or not.