One way of seeing that the "kool-aid" explanation doesn't exactly fit is that if you view Trump through a handful of frames, what he does makes a helluva lot more sense. One frame is that he is always negotiating, which is a very reasonable frame to use too -- he did, after all, write one of the most famous books on the subject. So when he says something like how Putin is doing a "great job" in Russia, it takes on different meanings depending on which frame you're using. If you're using a traditional politics frame, he's adding flame to the fire of the enemy. If you're using Level 1 Loser-thinking frame, he thinks Putin's a great guy and endorses him. If you're using a frame that has some level of understanding of Trump, he is using the statement in a forward thinking way. If you're planning on sitting across the negotiating table from somebody in the future, you wouldn't call his wife a whore and his son a wimp beforehand. You'd call him smart and sing his praises. You'd get his guard down. You'd get him on your side even as he attempts to not be. Likewise, if you're gonna be the US President and you're gonna deal with Putin, you'd be a fool to make such bad public statements about him that he enters the arena with snarling dogs.

When Trump says good things about Putin, people who have a >0 understanding of Trump think he's got a plan in mind, while people with Level 1 Loser thinking accidentally (purposely?) run nose first into walls.

A question is raised: how do we know that Trump is not being literal and that he has the country's best interest in mind? Well, we don't. But what we do know is that if he fucks his supporters over, they will fuck him over. His supporters don't want him bowing to Putin, losing to Putin, or doing anything to compromise the country in his dealings with Putin. It is reasonable to assume that Trump knows this too at the very least. He has shown signs of being extremely in tune with what his base thinks (one nifty example: his Pepe pose at the debate and retweet of the shop). The next step then is to understand who Trump supporters are. Fake News tells us they're all Russian spies and sympathizers. I guess that's why it's Fake News.