I am not from Laminar Research; just a flight simmer from down under.
For a single user flight simmer you can load X-Plane onto as many computers as you like. However, you can only run one arrangement at one time including your USB drive..
If you have a digital download then you have to be connected to the internet at all times as the software performs a silent background check to determine that you are using a single legal copy and also checks you are not running more than one copy at that time. If you do you will be locked out from running X-Plane.
If you use a dvd version the same situation occurs but disc 1 has to be inserted into your DVD drive at all times.
In your situation you are more than bordering on a professional version and you should contact Laminar direct starting with firstname.lastname@example.org setting out your proposal.
If you don't contact Laminar don't expect a response in this forum as we are all single user flight simmers.