Although it's worth keeping in mind that the stardates did follow a broadly upward pattern from season to season -- the first season went from the 1000s to the 3000s, the second was mostly the lower 3000s to the upper 4000s, and the third was almost entirely in the 5000s, with the animated series more inconsistent but still largely in the 5000s to 6000s. Then TMP was in the 7000s, the next four films were in the 8000s, and TUC was in the 9000s. Quite an inconsistent rate increase, but if you want to capture the feel of a certain season or era, it might help to pick a number in its range.
Does this mean that there is an actual stardate chronological view-order for TOS episodes?
No, it really, reallllly
does not mean that. Remember, we're talking about something that was intended by the creators of a work of fiction to give a general impression
of the passage of time. Like an impressionist painting -- if you look at it up close, you can see how rough the brush strokes are and how little it resembles reality, but you're not supposed
to look at it up close; you're just supposed to look at the broad strokes and get a general feel for what it's trying to convey.
There was absolutely no intention for the episodes to be watched in stardate order. How could there have been? This was the 1960s. They didn't have home video or streaming internet; they hardly even had reruns. The only possible order to watch the episodes in was the one the network aired them in -- or maybe, if you were lucky, the order that some local station aired them in when they bought the syndication package years later. And the producers had no control over either of those. So of course they didn't make the episodes with any specific viewing order in mind. The stardates were just meaningless numbers. They tried to trend them generally upward as the series progressed, but just roughly, just as a way of giving a broad impression, because they had no way of knowing what order the episodes would actually air in. The best they could do was try to make sure that the stardates toward the end of a season were higher than the ones at the beginning, and that the stardates at the start of the next season were about the same or a bit higher.
If you try to watch TOS and TAS in stardate order, you'd get some very strange results. The first episode would be TAS: "The Magicks of Megas-tu," followed by "Where No Man Has Gone Before." "Patterns of Force" from season 2 would be less than halfway through season 1. TAS: "The Practical Joker" would be late in season 1. "This Side of Paradise" would be immediately after "Amok Time," which seems an unfortunate juxtaposition both in terms of the Spock romance and the Kirk-Spock fight. TAS and season 3 would be largely intermixed. And there are five episodes without known stardates, so where would you put them?
I suppose it wouldn't be completely
nonsensical, except for "Megas-tu"; you could assume, say, that Chekov had been on occasional bridge duty in season 1, or that Chekov and Arex were aboard at the same time and were just on different shifts -- though why is everyone else on both shifts? Also you'd have to ignore the design changes in the bridge and engineering between TOS and TAS. If you left out TAS, just went with the live-action seasons, it wouldn't be too bad, aside from the "Amok Time"/"This Side" juxtaposition; in some ways it might make a little more sense than airdate order (since I don't think it makes sense in terms of the Kirk-Rand relationship for "The Corbomite Maneuver" to come after "Miri" as it does in airdate order). Still, I don't see any reason to prefer it over production order.