Teleportation would be easier in the long run, lol.
Seriously though any method is rife with engineering, geological, climate, weather, political, and financial problems to the point of pretty much being a never project.
The saddest thing about a RR from the lower 48 to Alaska is: It could be done - - - it just won't be done.
Wonder if the folks in Russia said the same things about the Trans-Siberian RR? Even if they did you will notice it was built and today is the main artery from Moscow to Vladivostok (Russian Trainzers please forgive my spelling if its wrong). Anyone think a RR from the lower 48 To Alaska wouldn't end up the same (an almost irreplaceable lifeline between areas)?
Ben