Follow-up: .PHONY and real file targets
Closing the loop on my Makefile question. Two things I had wrong:
1. If the target name isn't a file that gets created, mark it .PHONY or make will get confused when a file with that name shows up.
2. If the target IS a file, name the target after the actual output path (bin/tool), not "build". Then make can compare timestamps.
Rewrote it as bin/tool: main.c and added a .PHONY all that depends on it.
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Worth adding that .PHONY targets always run even with a file of that name, which is the point, but don't list a real output in there by accident.