"loophole" suggests a grey area between out-and-out dishonesty and a simpler exploitation of the rules.
My observation is that airlines will seldom pursue restitution after an event that challenges their terms and conditions. There have been exceptions, but these normally focus on serial offenders. Nevertheless, membership of an FFP puts shiny cards and miles in a vulnerable position.
Where a ticketing irregularity is discovered before the trip, airlines are likely to take preemptive action.
With a vacuum of information surrounding the OP's scheme, there's not much more than can be said.
The opening posts read like a tease from the "Trick It" playpen