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the original Winthrop sermon . . . was written to be a check on national pride.

I would say that that sermon was a challenge to walk worthy of our calling. To the extent that our ancestors did in fact live up to that challenge, that is a source of pride and a further challenge to us today to live up to their standard.
I think that Americans who denigrate America take so much for granted that it is historically absurd. I don't think that we would have very much liked some of our ancestors, in some ways - slavery is an example - but it has to be said that in the big picture the things we wouldn't like about them were things that were in fact commonplace to previous history and geography. There was slavery just about everywhere, during most of history. And arbibrary government.
The point is not that they were perfect but that in the long sweep of history they got us from there to here. We can take the lack of slavery for granted only because they sorted it out, painfully. It has been said that Lincoln was a racist, and I don't doubt that for an instant. I think everyone, pretty much, was racist then. The thing that is unusual about America is not its faults but its clamorous discussion of - and systematic amelioration of - its faults.
You mentioned Japan. It's not unusual that - in contradistinction to American practice - you aren't considered to be a member of society just because you were born in it. You want to become Japanese? Fine - just ~~go to the Embassy and apply for a green card and naturalization papers after three years~~ become related to the Emperor.
Someone told me he was a Turk. He said it with a thick German accent, because he was born in Germany. He was a Turk because his parents were Turks, even though he was born in Germany. And yet because he was born in Germany and went to Turkey after he had learned German, he was not really accepted in Turkey either.
That "Turk" now considers himself a New Yorker. In New York, unlike Turkey, no one gives a second thought to the fact that you have a German accent. In New York , unlike Germany, racial distinctiveness has very limited (if not zero) influence on how you are viewed and what you can aspire to do.

I don't think that we would have very much liked some of our ancestors, in some ways - slavery is an example - but it has to be said that in the big picture the things we wouldn't like about them were things that were in fact commonplace to previous history and geography. There was slavery just about everywhere, during most of history. And arbibrary government.

Slavery was actually mostly eliminated in Western Christendom between 1000 AD and the Renaissance. In this sentence are you saying our current system of government is arbitrary? That's my take on it, especially when it comes to the friggin' Supreme Court. Most everything governmental has been nationalized or internationalized, and I think certain conservatives' praises for the nation simply reinforce that problem.(Hey, speaking of which, Winthrop wasn't speaking of America but just his colony, right? So it seems his city upon a hill is even more wrenched out of context.)

Also, in an odd similarity with some leftists, I don't think much of assimilation. I still think of myself as Irish some 100 years after my last ancestor arrived in this land, and what isn't Irish in my ancestry is otherwise Celtic. The erasure of ethnicity in my mind is a bug and not a feature of American life. I don't like homogenization in general, but American assimilation in particular treats the nation's borders as one big River Lethe--all who pass through to stay must forget the past. One can even twist the phrase "Novus Ordo Seclorum" to justify such amnesia. Yeah, not everything should be remembered, but there is plenty that shouldn't be forgotten.

The issue is politics. Like most on FR, I am a paleoWhig. I believe in the Constitution as written and amended, both for tradition and because it institutes a highly pragmatic system, validated by history. I respect the fact that I can't have my own way on everything, and am grateful for a system which provides good enough government.

I once thought of myself as a whig, but I think I might be a Tory poseur, now. :) Anyway, I like the constitution well enough, but I think it has become simply a paper obstacle to either the General Will or the Will of the National Ruler, in the service of which legal arguments are manufactured. There's not much reasoning going on. The constitution has regrettably become an Ink-Blot test where you see what you want to see--it's even explicitly stated in Supreme Court jurisprudence now. In my eyes, it is lamentably no longer the charter for the government but simply a challenge for creative lawyers to overcome for fun and profit.

Also, the "good enough government" of compromise tends towards the lowest common denominator, and the cultural onslaught of the left has tended to make that common denominator lower and lower. Heck, even conservatives do so now: we're not a "Protestant Christian Nation" as the nativists insisted, but instead a "Judeo-Christian nation," to include the Jews and the Catholics. Right now some Muslims are even trying to get their name into that hyphenated adjective!

Frankly, I'm having a hard time distinguishing the current American system of government from a well-organized band of robbers, from the President down to Joe "Regular Voter" Citizen. Of course, the Soviet Union was a badly organized band of robbers, which might be even worse, but hopefully that's behind us now. Here's a passage from Augustine that presently haunts me:

"Remove justice, and what are kingdoms but gangs of criminals on a large scale? What are criminal gangs but petty kingdoms? A gang is a group of men under the command of a leader, bound by a compact of association, in which the plunder is divided according to an agreed convention.
If this villainy wins so many recruits from the ranks of the demoralized that it aquires territory, establishes a base, captures cities and subdues peoples, it then openly arrogates to itself the title of kingdom, which is conferred on it by the eyes of the world, not by the renouncement of aggression but by the attainment of impunity."
-Augustine, City of God Book IV Chapter 4

So much government, no matter the party, is simply divvying up plunder among one's associates, without regard to questions of truth or genuine human goods except insofar as they hinder the efficiency of any plunder's flow to one's allies. I'm in a very-pessimistic-about-politics mood this week, so hopefully this feeling will pass. I would appreciate it if somebody here can help disabuse me of this feeling. I've promised myself not to give up on the American political system until I attend a county party caucus, for fear I'm simply believing the sensationalistic prophets of doom in the media and pundit classes.

Thanks to you both for writing, I haven't had a discussion like this on FR in some time.