Predict: Which of these states will vote Republican in the next 20 years?

[Skill and Chance]

Incorporating trends, this is my best guess of what a reverse 2008 or reverse 1996 scenario would look like for Democrats.  One or the other is bound to happen within 20 years:

Note that relative lack of safe D states.  An R winning with 55% would have an excellent chance of 400+ EV.

[Skill and Chance]

For reference, I think this is the best possible case for a generic Democrat.  Hillary might make the Clinton-McCain states toss-ups if she is doing that well nationally, but I don't think anyone else could.

[Skill and Chance]

You really start to see the gap in safe states when you get out to Reagan/LBJ level landslides.  The states I am completely confident will not vote R are the 5 that would have held up in a 60/37 Romney landslide:

And I would be completely confident that these states won't vote D, because Obama doesn't even carry them if winning 60/37 over Romney (giving AK and LA to Obama with <50% because of 3rd party support):

[Skill and Chance]

Voted only New Mexico. I'm betting that current polarization means a 2008 Obama-style victory will be roughly the max number of EV's for either party over the next 20 years, but I'm also betting that Republicans will move to the center a little bit and do better in the Midwest within the next 20 years.

A more interesting question imo is which states will vote more Republican than the national popular vote in the next 20 years.

I bet an incumbent running in a booming economy could exceed Obama 2008.  I would say the modern upper bound is somewhere between Clinton '96 and Ike '52.  Of course there could always be a weird 3rd party situation.