A lot of the explanations for the cloaking device's earlier manifestations seem to suggest that Kirk, Spock, and presumably the rest of the Federation population would have been familiar with the fine details of Earth's first Romulan encounters. Why?
The way ENT portrays it, invisibility is a veritable
trademark of the Romulans in the early encounters - perhaps not completely unique to them, but definitely characteristic of them. If it remained so in the war that followed, it would be intolerable that future officers not be aware of this. They might have forgotten that Romulan ships had birds painted on them, so that only Stiles would remember this detail (although it would be a bit like forgetting that the Nazis used the swastika!). But from the point of view of a 23rd century starship commander, the
only thing worth knowing about the Romulans would be "the enemies who flew invisible ships". That knowledge should survive a century of silence...
In that sense, it would help matters ginormously if it were plausibly established that Romulans no longer were capable of any sort of invisibility during their big and memorable war. And I don't mean that modern 2160s sensors would have defeated it - I mean that people would no longer have had to reach for their technobabblerizers and gadgetaboobs when the enemy became invisible in that war; that the enemy no longer
would become invisible; and that the very concept of invisibility to the Mk I Eyeball would be forgotten because it played no role in the war.
There never was a war with the Borg before "BoBW", so the data on them would only have passed through a small number of specialists and freaks. There was a (supposedly) big and (supposedly) important war with the Romulans, though - and if that war had featured invisible enemies, it would certainly be remembered for its uniqueness. Not just by a few analysts, but by every last civilian who read the headlines about invisible enemies and cowered in fear under his or her bed as the result.
Of course, it's still possible that
a) the Romulan war was neither big nor important, and the public never got excited about it, and/or
b) invisibility in its more primitive forms was commonplace between 2150 and TOS, perhaps being regularly used by Klingons who got possession of the tech in ENT.
In the first case, a lot would be explained about the seeming ignorance of anybody but the personally involved Stiles and the walking computer Spock on matters Romulan - but nothing would explain why Commander Hanson, specifically tasked with monitoring the Romulans for months at an end, would not be intimately familiar with their history of invisibility devices. In the second case, it would become all the more understandable how our heroes see nothing wrong with the fact that a Klingon vessel (originally never seen on screen) can catch them with their pants down in "Errand of Mercy" - but the pronounced amazement of Kirk at simple Mk I Eyeball invisibility, and Spock's denouncing of the possibility as theoretical only, would remain unexplained.
Timo Saloniemi