The critical timing is Tchdh. To guarantee no bus contention, the CPU drivers have to deassert before the bus buffer is enabled.
Is the FLASH the only device on the external bus? You would normally use Chip Select gated with R/W to drive bus buffers, and only drive inwards on Read AND Chip Select.
Watch out for Interrupts. They run a "CPU Space Cycle" on the external bus. If you have the external buffer defaulting to driving the bus when there isn't a Write Cycle then this might cause problems.
Find the sentence in the SIM chapter that says "If multiple chip-selects are to be used to provide control signals to a single device...". You can program multiple chip-selects to assert simultaneously as different control signals for the same transfer. You might be able to program a spare chip-select or two to generate the buffer control signals.
In general, the bus interface is synchronous. Signals transition after the clock edges in the diagrams. The timing values that you are looking at that seem to be contradictory are the "worst case delay buildup" with the first signal running late and the second signal running early at worst-case capacitive loads and so on.
These chips have been used in designs where there are more memory chips than the CPU can driver on its own, therefore requiring external bus buffering. It would be worth trying to find the schematics of any development board designed like this to see how they handled the external bus buffering logic.
Look at Figure 1 on this diagram. I'm asking "why are they tying CS and RW into that gate?". Answering that might help with your question.
http://robotics.ee.uwa.edu.au/eyebot/doc/DataSheets/MC68332Tut.pdf
Tom