"...and I would call that poor urban planning."
Hindsight is 20-20. It is easy to dismiss the rapid development of our urban infrastructure (across the country) as poor urban planning. The fact is, most of our cities were developed on a grid system after the propagation of the automobile. It is poor planning in the idea that previous generations did not understand the finite possibilities of our energy sources. Cities that grew organically over hundreds and thousands of years are constructed and planned on a human scale, and it is a natural progression to move back to such density and development as we learn more about our world (encouraging walking and biking for healthier lives, reducing dependence on the single person automobile).
I guess I just take issue with an outright dismissal of the Anchorage planning process (see: Anchorage 2020, the municipalities comprehensive master plan adopted in 2001) based on a single comparison to Portland. That is just like comparing apples to oranges - neither community has the same history or socio-economic background, the planning process of either is often mired in a quagmire of bureaucracy, shifting political strata (each new mayor dismisses previous commissioners and department heads, changing long range planning with every new administration) , the demands of the populace, and the needs of the time. Portland has a population density 23 times greater than Anchorage (~4,000/sq.mile versus ~171). There is a hierarchy of needs that doesn't make sense when it comes to public transportation; it's one of the reasons our buses in town run well below capacity. It is impossible to compare the two cities based on this alone.
I'm with you on the fact that Anchorage is in an unfortunate place for the long term future. The city grew pretty organically in an automobile world with a populace that demands individuality (land, car, etc). It's the reason there is still actual debate on a billion dollar bridge. Someone here earlier mentioned the Anchorage bowl 'running out of land,' which is preposterous in the idea that we have blighted neighborhoods and shitty areas ripe for higher density redeveopment. That will move us to a more sustainable future.
One last note on light rail - you need connectivity to make it work. What do you do when you get off the train? Awesome if you're just hopping from the airport to downtown, as some business travelers would. But what about everyone else? Take a taxi? You need a consistent and reliable system and a dedicated population (population density!) to make it work. It's not as simple as just adding one link. You should look at Anchorage 2020. It pretty much highlights the idea of redevelopment being the way forward for the city, and echoes principles of good planning and design.