Yes. That'll be a big temptation for Trump. The major basis of his 2016 campaign was fear, and if he's struggling in 2020, it's going to be very tempting to get us involved in a war that will drive up fear levels and make people reconsider a change of regime.
Me, too. He's a really good guy -- smart, funny and deeply informed. Of course, as with all the females on the Democratic side of the aisle, his wife developed a reputation for being a "holy terror." That's an archetype that, for whatever reason, our culture feels the need to shove Democratic women into -- Hillary Clinton and Michelle Obama are others who found themselves with that label.
Anyway, I'd like to think that Kerry lost because his campaign was a mess, since that would make me more hopeful about 2020. But I actively campaigned for him up in New Hampshire in 2004, and I didn't see it. It was a well-run organization. It really came down to the fact that the kind of people who voted for Bush just didn't give a crap that he was hurting America, because they had their war to enjoy vicariously, and besides they were scared to death that some gay guys were getting married in Massachusetts.