Let me put this in other terms.

In the world you're talking of, the surveillance happened in person, within a village, with approximately one book per million inhabitants[1], with a typical travel and data transmission speed of roughly 3 mph, a peak of perhaps three times that, exceedingly low literacy (~5% in villages, perhaps 25% in towns[1]), and very low data transmission rates: verbal recitation. Though perhaps with a fairly fast interactive natural-language query system (e.g., interrogation).

It was possible to escape that domain by travel, either temporarily or permanently, as little as 10-20 miles might suffice.[2] As late as the 19th century in the United States, it was possible for a well-connected and politically connected man to lead a double life.[3]

As to the detail of the data, your question begs credulity in light of what I've stated above. The rates of data accumulation today simply surpass all of recorded history. Something like 90% of all recorded data come from within the past decade. As of 2007, 94% of all information were in digital form.[4]

You assert, without proof or evidence, that there is no difference between digital information stored across servers, and the disaggregated wetware knowledge of your immediate associates. I pose as counterexamples Uber's Greyball program, which in realtime tied multidimensional characteristics of a user's Uber account, available hardware information, and social networking profiles, amongst other signifiers, to determine who was or wasn't a possible government employee, and to literally change their perception of reality as a consequence.[5] Thirty years ago, your magazine subscriptions might have been shared amongst marketing organisations, sixty years ago, state intelligence services might have had access to them. Today, your Kindle reader tracks what passages you've read within books, and every website, and its third-party scripts and cookie shares, track precisely what you've read online.[6][7]

That is straight up the definition of "Orwellian"[8]

Size, scale, and rate, matter. As a noted expert in the field observed, "quantity has a quality all its own".[9] Even gradual changes lead to phase shifts past a transition point, some sudden, some not. A small group of observers -- the few hundred of a mediaeval village -- is well within the Dunbar's limits of our brains,[10] and is subject to direct observation to boot. It has little capacity to keep a permanent record of its information, or even, particularly, to correlate observations from different observers. It cannot spread that information throughout all of humanity (some seven billion three hundred million souls, presently), nor can it act from out of the blue based on that information. It is a petty oppression, not a grand one.

Today's digital information attacks are difficult, often impossible, to precisely attribute.[11] Those who build information systems do no, will not, and ultimately in all likelihood can not protect them from attacks or subversion.[12] Data is described, by seasoned experts in the field, as a toxic asset.[13] It persists, can be used for fraud, blackmail, character assassination, to micromanage individuals lives (a supreme denial of liberty), and more.

Your arguments, or should I say assertions, are supremely unconvincing.

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Notes:

1. Buringh, Eltjo; van Zanden, Jan Luiten: "Charting the “Rise of the West”: Manuscripts and Printed Books in Europe, A Long-Term Perspective from the Sixth through Eighteenth Centuries", The Journal of Economic History, Vol. 69, No. 2 (2009)

2. Though, yes, there were strong limitations on such travel, see the Vagrancy and Poor laws of England, as examples, which applied to labourers. Nonetheless, a skilled craftsman, scribe, or professional could and many did, travel throughout Europe, particularly when the political heat got too great at home.

3. Geologist Clarence King, whose professional colleagues had no knowledge of his marriage, and his black wife, who thought he was a Pullman Porter, comes to mind.

4. https://www.sciencedaily.com/releases/2011/02/110210141219.h...

5. https://www.nytimes.com/2017/03/03/technology/uber-greyball-...

6. http://www.ibtimes.com/psst-your-amazon-kindle-spying-you-92...

7. https://www.eff.org/deeplinks/2009/09/online-trackers-and-so...

8. https://www.worldcat.org/title/1984-a-novel/oclc/905951412&r...

9. Though he covered his tracks well: https://en.m.wikiquote.org/wiki/Talk:Joseph_Stalin

10. https://en.m.wikipedia.org/wiki/Dunbar%27s_number

11. https://www.schneier.com/essays/archives/2017/01/why_proving...

12. https://www.schneier.com/essays/archives/2017/03/botnets_of_...

13. https://www.schneier.com/essays/archives/2016/03/data_is_a_t...