All of these states last went Democratic in 1964. Which one will be the first to go Democratic? Alaska does seem to be the obvious choice, but it's harder to guess which one would be the next to fall. Utah and Kansas were the 2nd and 3rd smallest wins for Trump, but the Dakotas seem more elastic, and might be more likely to go Democratic in a landslide. I'm guessing that if most of these states eventually do go Democratic in an election, Wyoming will be the last holdout, though Oklahoma could be as well.
My guess:
There's a chance of Utah going for an independent (McMullin?) if Democrats nominate a far leftist and Trump doubles down on being Trump by 2020 (with Pence, there's no chance of that).
Other than that, Alaska in the long run, but if it happens soon (2024 or earlier), maybe South Dakota instead?.