The Washington State Department of Transportation will demolish the viaduct, freeing up 26 blocks of urban land. It will be replaced with a street-level boulevard and 20 acres of waterfront public space designed by James Corner Field Operations. Soon, Highway 99 will traverse Seattle below ground in a long-delayed bi-level tunnel dug by the world’s longest boring machine after a prolonged political fight pitting governor against mayor that made Seattle the laggard in a trio of major urban highway teardowns, alongside Boston’s Big Dig and San Francisco’s Embarcadero.

But this transformation stands to be a painful one. The highway closure kicks off a two-year stretch that City Hall calls the Period of Maximum Constraint and everyone else calls the Seattle Squeeze. The viaduct’s 90,000 cars are losing their north-south waterfront right of way. There’s mass-transit help on the way, in the form of Seattle’s massive light rail expansion, which is set to open a key northern extension in 2021. In between, downtown commuters and residents will contend with a ferry terminal rebuild, a convention center expansion, 600 daily buses moving from the downtown transit tunnel onto surface streets, a streetcar missing link on hiatus, and street closures related to the construction of the city’s second-tallest building.

The first three weeks of the Squeeze—known, somewhat apocalyptically, as Viadoom—are expected to be the worst, until the new State Route 99 tunnel opens on February 4. In anticipation of V-Day, local TV news has been running countdown clocks, and city officials are urging anyone who can to work from home, switch up hours, or take time off. Further amping up the state-of-emergency vibe, Mayor Jenny Durkan hired Mike Worden, a retired Air Force major general, to oversee the city’s response to the Squeeze. (His office did not return a request for an interview.)…

As with marquee waterfront-highway removals in Boston and San Francisco, the hope is that the viaduct’s demise can give downtown a waterfront worthy of Seattle’s setting. The design for the redeveloped space, by James Corner Field Operations, aims to string together several of the city’s major attractions, though some of the bells-and-whistles in the competition-winning design, like a swimming-pool barge and a downtown pocket beach, have been toned down.

At the same time, I could imagine many residents would want to know why this all seems to be happening at once. This is a complaint I have heard regularly in the Chicago area: why is there construction on multiple major roads at the same time that then makes it very hard to find alternatives? People can get the idea about the long-term benefits and still experience frustration at the day to day difficulties these projects pose.

Additionally, what are the odds that all the projects finish on time and on budget? Major infrastructure projects in American cities can end up with significantly larger price tags and seem to last forever as circumstances (and budgets) change. Again, these projects often need to happen but residents may perceive that officials and those involved in the construction do not care much for their time or pocketbooks.

Of course, an easy solution to all of this is to simply pursue these projects far before they become such boondoggles. That, however, is far easier said than done.