Philadelphia is also the first place I have lived where parking in the center median of major thoroughfares is normal:
https://www.google.com/search?q=philadelphia+center+median+p...
Speaking of, I live a block off South Broad Street (most of the images in the link) and not too long ago there was a marathon that required clearing of that street of all parked cars for its entire length. It _was_ well communicated, well in advance but you can imagine that if parking is tight when the street side parking _and_ the center median is chalk full of cars, relocating is difficult. I don't know if any cars were relocation towed, but I know the night before the event I still saw some cars parked on Broad.
I still think there are communications issues, the city should have a way for owners to find their car. But I also think it's a bit more complex than your first take. Communication is hard and at the scale of Philadelphia I am not too surprised that there are cases where things can go awry between all the various bureaucracies you have to interact with in something like this. I also think it's pretty reasonable that the lawsuit is looking to force improvements, not do away with the system.