So the Season 3 set is maybe the grand prize of the whole collection.
That's a hard statement for me to accept, thinking about Friday's Child and Kaplan's recording of Enemy Within, along with Adonais and Catspaw and City and extra struff from Amok Time. A lot of people love Duning's Metamophosis, too. But you've made a good case.
I didn't mean to suggest that season 3 had the only good stuff. I just meant that not only does it have many of the best scores, but it's the least represented season in prior releases, with absolutely none of its original recordings ever having been released before. So collectively, as a full-season set, it's got more long-awaited, never-released content than either of the other season boxes, including my all-time favorite TOS scores. And that makes it stand out as a part I'll be particularly glad to have, though I'm certainly glad for the whole thing.
In other words, the season 3 set is the one that has the highest proportion of "Oh my god I've been waiting all my life for this and I never thought I'd get it and here it is squeeeeeeeeeeeee!!!"
It's interesting that Fried is playing the oboe at the upcoming event, because the oboe is featured at some moments in the Paradise score. I found myself wondering who played oboe during the recording. Did the studio orchestra have woodwinds, or did Fried play it himself?
I've also wondered the same thing about the rolling piano in the Enemy Within score, whether it was Kaplan.
If they were conducting their own scores, I doubt it, unless those bits were recorded separately.
And the studio orchestra certainly did have woodwinds. One thing that strikes me about '50s/'60s TV/film music compared to more recent scores is that the bassoon seems to have fallen out of favor since then. A strong presence of bassoon and other winds is sort of a trademark that distinguishes older scores from more modern ones, at least to my ear (although Shirley Walker brought back a lot of vintage orchestration in Batman: TAS
and The Flash
The preview image at TrekCore
includes a glimpse at the orchestra list for "City on the Edge of Forever," and there are a few woodwind performers listed.