Here is a more straightforward but frustrating version of the same problem.

Suppose Jack and Jill are both private pilots and suppose neither is night
current.

It is legal for each one to go up solo and do 3 night landings for currency.

It is NOT legal for them to go up together and each do 3 night landings for
currency.

Yet clearly it would be safer (although not legal) for them to go up
together to do the 3 landings so that a night-inexperienced pilots has
another set of eyes helping him/her out.

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Richard Kaplan, CFII

www.flyimc.com