If the 8088 had used all but one 256 8-bit values as legal instructions, all your new instructions after that point would need to start with that unused value and then you can add a maximum of 256 instructions by using the next byte. End result is 511 instructions can be encoded in 16-bits.
If the 8088 had used all but one 256 8-bit values as legal instructions, all your new instructions after that point would need to start with that unused value and then you can add a maximum of 256 instructions by using the next byte. End result is 511 instructions can be encoded in 16-bits.
Ah right! I forgot about that.
So you either have to pad all instructions in all previous binaries, or reduce the amount of available instructions in the arch update.