I just skimmed the Wiki list... man, there are a lot of those suckers, aren't there?
Speaking as a TOS reader, I've read all of the Bantam original novels... order is not an issue at all, so pick the one that most strikes your fancy. Same goes for the unnumbered Pocket books, of which I've read everything up to "Probe." I can recommend all of the books above, but if I was going to be crazy enough to recommend any single book out of those, I might pick "Prime Directive" as the first book I'd try.
Fortunately, Paramount maintained high quality throughout the TOS books, so all of them are good reads (though the episode novelizations are a bit dry).
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