Quite a coincidence that this subject should come up just as I make a personal discovery on it !
Crank seals must be fitted with the open side (recessed) facing towards the outside of the engine, towards the gearbox oil on the right side, and towards the generator on the left.
This is of more importance the bigger the engine capacity, it is imperative on an open class machine; let me explain ...
I have found the vacuum in the two-stroke crankcase far exceeds the compression, maybe it can be due to effects of the expansion chamber I don't know. At high rpm the vacuum through the carb is ferocious, now if you close the throttle at high rpm the pumping action is still continuing and drives the vacuum through the roof, it can have a big effect on the crank seals.
Face it, you would rather have some loss of crankcase pressure 'out' through the seal than air being sucked in causing a lean air/fuel ratio right?
With the seal recess facing inwards, the vacuum can lift the seal lip away from the crank, with the recess facing away from the engine, vacuum will cause the seal lip to be sucked tighter onto the crank.
Smaller engine may not have the vacuum strength to lift the seal lip but a big engine will.
I found this on my Honda CR500RE, even with new crank seals, at high rpm & part throttle, when the crankcase vacuum is at its strongest, the seals were leaning-out the air/fuel mixture, and doing it inconsistently. Sometimes the gear oil would partially restrict the leak making me think I am going crazy!
The vacuum leaking through the gearbox seal was also bring in dust through the gearbox breather, making the gear oil dirtier quicker.
I have since rotated the seals (new ones again) and all is well.