Enterprise doesn't show a particularly disastrous first contact (unless Picard is talking about the Temporal Cold War or something), and I don't think the conflict from Discovery really counts.
And indeed neither would have been much improved by the implementation of pre-contact surveillance. Sure, the heroes got the Klingons' number wrong in certain ways, but this actually helped Archer not get killed immediately... And the UFP did have all the intel it needed to help out Burnham, only it a) hadn't reached Georgiou, and b) just made the matters worse.
Which brings me to my argument: The disastrous first contact with the Klingons is the Vulcan-Klingon contact. They already know each other in Enterprise. Discovery goes into detail on when they met and how, and it sounds pretty disastrous. This is 2016 (351 years is a better fit for "centuries ago"), and we learn about the Vulcan Hellos that succeeded the Klingons attempt at expansionism.
Were the Klingons expansionist, though? Or were the Vulcans? It was a Vulcan vessel intruding into Klingon space that Sarek says triggered the incident that started out the Vulcan Hello practice.
Nothing about Sarek's story directly establishes how preceding covert surveillance would have helped there. But at least the choice over whether to spy or not would have been the Vulcans' if they were the invaders.
I'm guessing Michael glossed over the fact that the Klingons and Vulcans spent decades at war (or, just, casually greeting each other with Vulcan Hellos and Klingon Good Days). Decades after 2016 leads dangerously close to First Contact (the movie, not the episode) times.
What
was established in "The Vulcan Hello" was that the Federation
never had been in hot war with the Klingons before that day. So Picard's contact absolutely must precede its founding in 2161 - by decades at the very least.
To let it precede 2016 as well is still an option. And an incident in even more distant past might in theory feature elements where pre-surveillance actually makes a difference. But there we run into the problem that Vulcans are our prime candidates for advocating pre-surveillance (since they factually do that very thing in ENT), yet any Vulcan-Klingon disaster preceding the 2016 incident would both dilute that incident (why should Sarek bring up a meaningless single-ship incident when he has a whole war to refer to?) and call to question whether the Vulcans had in fact learned anything (since if they did do their homework, they'd have said Hello in 2016 already).
Is there any way to squeeze more hints out of "The Vulcan Hello"? Sarek there says the Klingons have been in internal disarray for "generations" as of 2256, therefore not a credible threat (and thus probably not in hot war with Vulcan, either). How long is a Klingon generation? Klingon individuals apparently
live long unless violently killed, much like Vulcans. But we have little data on how Klingons
breed. Worf got Alexander pretty early on, but was that an atypical mix of a tradition-minded male and a devil-may-care female hastening the evitable? We get minimal information on the ages or descendants of other Klingon characters - and the looks can deceive in both respects!
By 2063, the Vulcans will probably have militarized to face on this existential threat, and will certainly be looking for allies/client states in the buffer zone between Vulcan and Qo'noS. What planet lies dangerously close to the Klingon Empire (per Enterprise): Earth.
...Although ST:TMP and the like would rather have us think that it's Vulcan that is en route from Earth to Klingon space! Which is how the modern onscreen maps put it, too, even if there's plenty of room for argument.
Vulcans seem hard pressed to fight Andor in the 2150s. A nation fighting on two fronts, one of them invisible? A nation weakened by a past conflict? A nation that has wisened up and now just intimidates and manipulates, with a Potemkine fleet of limited numbers?
By getting to the Earthers first, almost minutes after warp discovery, the Vulcans have expanded their influence and gained a foothold to fight back against their most dangerous foe. They're the ones who established first contact rules and non-interference doctrines.
And apparently followed those themselves with Earth, spying on us since at least 1957... An act
not prompted by the 2016 encounter, then - unless there's more to this vehement denial of time travel by the Science Directorate than meets the eye!
The Andorians probably were a similar Vulcan client race.
Or then the Vulcans would have wanted them to be, hence the conflict.
Of course, it goes without saying that the Vulcans were entirely influenced in all of this by the Romulans, seeking secret hegemony over the region. But that's a tale for another day.
Or then there's no real Vulcan-Romulan rift, and
both sides of the border are analogous to North Korea, by the very nature of the peoples there...
Timo Saloniemi