We bought Alaska for two pennies an acre; I don't think Congress has enough left in the Treasury to pay the capital gains tax on the transaction, given the increase in real estate values.
Of course, the Fed could just print more to pay those taxes; they've got a lot of recent practice doing that, I s'pose.
Definitely throw in Hawai'i - the day after the SCOAMF moves into that $35 million retirement home that's being build there for him. And we could sell Puerto Rico, too, while we're at it.
As for the flags? I don't go for the whole change-the-star-count-with-the-state-count deal. I say we go back to thirteen stars in a circle and just stick with it. Besides, do we really want to have to redo the flags every time another state secedes? How will all those eight-cent-an-hour seamstresses in Red China who make our flags possibly keep up with the revisions?