I've worked closely with executive protection and corporate security. Despite the occasional screw up it is a "known thing" that hedge funds have been tracking tails for years and rent jets for sensitive meetings. Hedges have also caught on to swapping planes during a refueling stop (Colorado and Nashville were common for this).

Companies with multi-plane fleets usually have at least one "anonymously" registered via Aircraft Guaranty or Wells Fargo Trustee Services.

(Feel free to email me if you'd like to talk more about this offline).