You raise a number of extremely important factors to be taken into overall consideration.
Just a few thoughts on issues you've raised:
1. In regard to Alaska natives...Alaskans tend to view themselves as an independent, almost pioneering people and are generally suspicious of anyone from "the lower 48." They have a tremendous sense of state pride, a factor which could weigh decidedly in our favor, or work against us, depending on how we approached them. At the same time though, they're used to receiving "refugees" from the lower 48, and particularly noted a rising trend in migration to Alaska during the Clinton years (a source of pride for them). They would be suspicious of us, but would likely receive us in time if we showed our determination to become Alaskans and shied away from attempting to impose "outsider" ways on them (ie: the way things are done in the lower 48).
Also, as you mention, the state's aging population is a growing concern. I read the Anchorage Daily News and Fairbanks News-Miner online quite often, and I've seen a lot of concern being expressed on the fact that "all the young folk are moving out" in letters-to-the-editor, etc...The stats that you cited may help work somewhat in our favor there as they indicate that the vast majority of AK residents were originally "outsiders." Having once moved there themselves (likely to escape life in the lower 48), such persons would probably be more receptive to us. On the other hand, we'd also have to factor in how long those transplants have been living there.
2. In regard to the NEA, here I think you've identified what will likely be one of the top three sources of opposition to us, if not THE top. The NEA is a well-organized, very vocal, and very effective special interest group. If we disclose plans to privatize public schools, we'll effectively be starting a war, the severity of which will probably amaze us in the long run. The NEA absolutely cannot afford to have a state government demonstrating successful alternatives to the current nationalized public school system. They'll pull out all the stops to oppose us, including marshalling all of that "no child left behind, invest in the future, education is not just for the rich" rhetoric. Congressional liberals will side with them and enact whatever form of coercion necessary to keep us from succeeding. And our arguments that it is our business and no one else's will not disuade them. South Carolina tried arguing that with regard to the Confederate flag, but the issue was still the subject of a national "dialogue," and even became an issue in the presidential campaign.
Education reform like the FSP has in mind, even restricted to a single state, could be a fight like none other in recent memory, closely followed by dismantling welfare and environmental de-regulation. I support all of these reforms, but think that we're going to have to plan very, very carefully if we want to come out of the battle better off than Custer did at Little Big Horn.