I'm kind of mixed: optimistic in the sense that I don't think we'll still be using the Electoral College in 2050+ but pessimistic in that I don't think the compact will succeed soon. If I had to guess, I'd say the 2020s is the earliest it would happen if there's no 2000-like situation in 2016. There's too many Democratic-controlled states going slow and too many Republicans blocking it in D+ states like Wisconsin or Pennsylvania for it to happen in the 2010s. I think the 2020s could expand the map with immigration reform, a potential supreme court decision overturning felony disenfranchisement laws, and shifting demographics. Those things could really shift the balance of power in states like Arizona, Georgia, Florida, etc which can offset Wisconsin or Pennsylvania or Ohio.
I think your map of least resistance is pretty good but I wonder about Pennsylvania. Pennsylvania doesn't have initiatives and Republicans have a pretty good lock on the PA state legislature and, when it comes to winning the Presidency, Pennsylvania is a top state for Republicans to go after so I don't think you'd see consensus for joining the compact there. After all, they were the first people floating that allocating EVs by (gerrymandered) congressional district idea back in
2011-2012. They seem keen to exploit Pennsylvania's relative position.
Things are pretty fluid but there is a path where Pennsylvania (20EV) could be swapped for say Maine (4EV-LePage loses reelection in 2014?), New Mexico (5EV-Martinez is picked as 2016 Republican VP?), Nevada (6EV-Sandoval runs for Senate in 2016?) and... damn it's looking pretty tough from there considering Gov. Branstad looks safe in Iowa and the gerrymander in Virginia. Maybe Arizona (11EV) through an initiative? West Virginia Democrats could really save the day if they joined the compact in 2014 while they still have a D-trifecta...