I would say that subsequent orders to the same unit count as 2nd orders.
As an example:
A unit reduced from 3 stands down to 1, and close to the enemy (-3 command penalty) is issued an order by a Ld9 general with the crown of command.
This is the general's first order of the turn, so giving orders to that unit tests against a Ld of 10.
Assuming that passes, the general can attempt to issue orders to that unit again, but this time (assuming that unit is still for some reason close to the enemy) would test against Ld 5 (Ld9, -2 for the 2 lost stands, -1 for the enemy proximity, -1 for the second order to the unit).
100pts is expensive, but all magic items are overcosted in Warmaster, and things with ongoing effects (eg. 1 order per turn) are very rare. Also, in Warmaster movement is vital, and the unmodified Ld10 thing almost guarantees one order per turn goes through regardless of the situation. That's pretty big.