What's confusing you is that the use of 'unless' in the original sentence of post #1 is a special case where the phrase 'unless, of course' is used as an afterthought. Because it's an afterthought, you should treat it as a new and logically distinct utterance because it does not affect whether the previous part was true. In fact, importantly, it contradicts what was said before. This contradiction is what you're struggling to understand.
Let me write the passage in a different way, to show you what I mean:
I couldn't have got to the meeting. Unless, of course, I had caught an earlier train.
I've written it in two separate sentences to show the meaning of the first utterance more clearly. The meaning of the first utterance is not logically connected to the second. By reading the first sentence, you know that it was not possible for the speaker to go to the meeting, and so you know he didn't go. The second sentence is only an afterthought, where the speaker qualifies what he has just said. If this afterthought were to be written in its logical entirety, it would look like this:
I could have got to the meeting if I had taken the earlier train.
As per the usual logic of counterfactual sentences, you can hopefully understand from this that the speaker did not attend the meeting.
The original example sentence uses a dash rather than two separate sentences, which is fine. You could also use an ellipsis to do the same job:
I couldn't have got to the meeting ... unless, of course, I had caught an earlier train.