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I'll play...
The second one (school / remodeled in 2008) would be the one I'd pick because I assume abatement would have been done, the area it's in looks best and it seems like the most normal building. 54K would be a LOT of space to deal with...
It could probably be turned into a mixed use building with the commercial area maybe being something like a coffee shop or small restaurant since there's a park nearby and a larger street about a block away. That would be the art/dining/kitchen/music classroom area. The parking lot and basketball court area would probably provide enough parking to keep the city happy.
Now it's time to start defining an owner's living space. Take CL 140 and 142 and turn them into a huge garage with lifts and all that. Take the gymnasium and adjacent areas to the left down, stopping at the media center area, to provide physical separation between the commercial area and where someone lives. Then build a new exterior wall matching the style of the one facing the street however many feet into where those rooms used to be. That defines the owner's residence, easily 10K+ sq ft by the time old partition walls come down and new ones go up.
The classroom areas up from the office could be partitioned off into two additional large areas (3,000 sq ft? each?), basically turning it into a large triplex that would hopefully offset taxes on the place or bring in some extra income. I'd try and tie into the 1950s look of the building as much as possible instead of fighting it. The brickwork seems pretty nice and the large windows lend themselves to nice, open living space.
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'87 924S (Sold)
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