Woodward is more of a grand avenue than a High Street -- I don't think Columbus's High Street is a great analogy to it. Detroit's avenues were meant to resemble the wide Parisian arterials.
I was in Detroit last month and I can say pretty unequivocally that Woodward Avenue looks much more cohesive in person than it does on those street views. I'm not sure if that's due to the timing of the Street View photos, or if for some reason GSV doesn't really capture wide avenues very well. But it appeared that nearly every unoccupied lot between downtown and the Grand Boulevard was being built on. And this was after a year and a half of pandemic.
However, I do think/agree that Detroit created an unintended problem by tearing down urban fabric to widen the avenues. But, I don't think that this is a fatal flaw. The reason they did that in the first place was to make room for streetcars, interurbans, and vehicular traffic, and also the eventual implementation of a subway system. At some point the city planning lost its way and just erased everything else in favor of the traffic lanes. But I think it's pretty obvious if you drive around Detroit today that the city leadership is trying to get past its car fixation. They are converting traffic lanes to bike lanes in all parts of the city, which seems to have reduced the psychological width of a lot of the wide streets.
Anyway, back to High Street vs Woodward. A more accurate analogy of High Street in Detroit is probably anything that isn't a radial avenue. And just about all of them could use a lot more infill, including even the ones in the best of shape. But I don't think Cass or Second Avenues, or John R Street are exactly lightyears behind High Street:
Second Avenue:
https://goo.gl/maps/TeWSWjL6TE2QSXj17
Cass Avenue:
https://goo.gl/maps/NJUGKhy8R3MhusyC6
John R:
https://goo.gl/maps/U4hGTDtKXYryEmiB8
Again, not claiming any of those are as well developed as High Street at the moment, but these are the three streets parallel to Woodward Avenue through Midtown Detroit, and they seem more like the analogy of Columbus's High Street to me.