The idea is that if the voltage drops (say) 10%, then you can use a boost transformer to bring the voltage back up.
The problem is that voltage drop is not a constant; it changes with load. Unless the load is constant, the voltage drop will change. An ordinary boost setup can't compensate for these changes; so at light load your voltage will be too high.
If, rather than reducing the actual voltage drop, you want somehow compensate for it, then you would either need a transformer (or other converter) that adjusts to stabilize the output voltage, or you would need loads that tolerate and adjust for wide supply voltages. For example some lighting ballasts function perfectly well on anything from 120 to 277 volts.
However such compensation for voltage drop doesn't fix the fact that voltage drop is pure efficiency loss.
-Jon