The second crossing should be a toll bridge because it will be used almost exclusively by very few, but affluent, Juneauites. Let the few that are going to use the bridge pay for the bridge. Or better yet, why not run ferry service back and forth? That seems to be the stock answer for all the transportation problems that threaten Juneau's gated community status.
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When poor and middle income people want affordable access to Juneau they're told to go buy airline tickets or spend a few hundred dollars to put their car on a ferry. When wealthy families want a bridge of convenience, they expect it to be built right away and everybody should help pay for it.
I say build the road to Skagway first, then we can worry about building a bridge that serves only to shave off a few commuting minutes for the affluent from their homes to their favorite valley shopping centers.