^ First, I think it's definitely a moot point because of the current core - it's definitely smaller and for residential/hotel as opposed to what would be needed for high traffic office.
Second, I very much get you point on highest and best use from a transit/micro location standpoint. Definitely valid way to look at it. However, there is also how the market would view and value the highest and best use, simply from a level of interest from bidders/number of bidders (as far as what use they would slate for it), price offered per sq ft, etc in terms of this piece of land. It's clear to me that the market clearly thinks residential or residential and hotel is a better use for the high-rise component of the property than office (the demand for top tier office space - both existing building and proposed new construction - is much lower in the central loop/east loop (i suppose this would be around the eastern edge of the central loop) than in the W Loop and the special 'view from, view of' high profile, riverside locations. There is enough competition from landlords (Top-tier supply) for large A credit tenants in the N/S Wacker Corridor (including within 1-2 blocks of N/S Wacker), and those special view parcels - think 300 N LaSalle, River Point, 150 N Riverside, Wolf Point, etc), to more than satisfy all the demand that's out there - and more. But, there's loads of current potential from a demand perspective for development of residential and hotel in the central/eastern loop (of which block 37 is a very prime location) right now.....
I definitely don't think that markets are always right however........clearly those economists who worship efficient markets as a reality got their intellectual clocks cleaned throughout the last economic cycel or two, and those who have stuck with it despite all the daily contrary evidence will be judged as fools by history....
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It's simple, really - try not to design or build trash.
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