I would design the wall for the condition with 5 feet of extra excavation - First, so that you can install the drain; Second, so that the drain can be repaired in the future. I would extend the facing to the bottom of drain trench excavation so that the facing never gets undermined and hangs eccentrically on the sheeting. Also, 5 feet sounds awfully deep for the drain pipe. Can't you just use weep holes through the precast facing just above finished grade? However, it is common for some state DOT's to require the wall be designed for an additional 5 feet of height to accomodate future utility excavation. Can you just use weep holes through the precast facing just above finished grade? Is there that much water that it needs to be collected?
How high is the finished wall? How much ground water is there? Is there any special reason you are using steel sheet piling? Many walls are built with driven or drilled-in soldier beams, lagging, and pre-cast or cast-in-place concrete facings. Frequently, a wall needs to be tiedback if the soldier beams or steel sheeting can not cantilever. This would probably be the case if you add the extra 5 feet of excavation.
I would not worry too much about cutting weep holes through the sheet piling if they are near the neutral axis of the sheet piling. I would be more concerned with making a proper connection at the sheet pile wall so that water can properly get into the drain pipe without clogging or loss of soil into the stone backfill behind the precast panels. You may want to use slotted pvc pipe installed through the cut weep holes or perforated PVC pipe wrapped with a geotextile. These pipes could then be extended to the outlet drain pipe.