That must have already been covered somewhere along the line, else Data would never have been allowed to join Starfleet in the first place.
Not very likely. After all, "Measure" makes it clear that there is no working definition of "sentient", and the resident experts in cybernetics, law, medicine and philosophy struggle to come up with one. It could hardly be one of the entry criteria for Starfleet, then!
No organization today requires sentience from its employees, chiefly for the above reason: coming up with a definition would not only be difficult, it would be counterproductive, since it would always end up excluding some folks the employers want included and vice versa.
Say this situation were real. The real ship owner had come to Picard's time to observe this event (Which is likely what he was planning to do, because I doubt the guy we got knows enough about the ship to have planned out that trip on his own. It was probably already programmed)
...It appeared close enough to be observed by the heroes. If it was to be a stealthy mission of observing the
Enterprise, it was set to fail (even a cloak wouldn't help because the time transit itself already triggered the alarms of the hero ship). If the original operator was interested in pulling a scam like the one we saw, though, this sort of programming makes at least some sense.
More probably, the original owner indeed had no idea the
Enterprise would be there, and was planning on observing/looting the planet while it was undergoing its big disaster moment. "Rasmussen" would simply read the registry of the ship off her hull and wing it from there. Funnily enough, he doesn't use the name of the ship when first arriving, just the bigger-font registry number. Fuck, he doesn't know Picard's name until deep into the episode!
So Picard grills the real time traveler in the same way, about wanting to know the outcome of his decision. What that guy should've told him is "Look Picard. I could only ever tell you what you did, as I know it, & if that outcome is unfavorable to you, you won't do it. Now setting aside what the consequences of that would do to me & countless others in my time line, perhaps eliminating us all, the other issue is that whatever you DO decide to do instead, could be just as unfavorable, & I know absolutely nothing about those outcomes. So you're just taking a different gamble. Ultimately all you're really doing, by getting me to tell you what I know, is trying to shirk the responsibility for what you're about to do onto me. You don't seem as cowardly as that, & shouldn't the gamble you take be the one you believe in & not the one I believe might work? Man up, sir."
And Picard would just respond with "You fail basic logic, buster. Me knowing that one choice leads to a bad outcome is already an improvement in absolute terms. You telling me
how things fail when I choose that way will help me further. Now it's your time to choose: is it gonna be truth serum or telepathic probing? I might also do old-fashioned torture just for fun."
Timo Saloniemi