ks0108s are really dumb so the commands or data accesses are usually very fast to execute.
Usually they are ready before you can generate the next command or data access.
I've occasionally seen them take and extra 3-4us to respond but that is not the norm.
I would think that ic2 should not have an issue overrunning the lcd as the byte transfer time at 400k bits/sec is 20us.
Even if you bump the i2c clock to 1Mhz, a byte transfer time is still 8us
and you have to transfer at least 2 bytes to control the 16 bits on the output port
plus you still have I2C START + ADDRESS + STOP overhead.
--- bill