: How far apart can the dots be? I've written enough to know the kind of writer I am, my voice, my style. I am often accused of making the reader work too hard to put the plot points together.

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Twilight Zone had an episode similar to this scenario, but they covered a wide array of the bizarre.

The issue of lost time - one night covering the months or even years it takes for conviction and appeals to be exhausted - that is one you might need to explain a trifle.

Supernatural agency in the form of the devil as barkeep does explain it, but that might be something you want him to realize later.

Stories that begin in a bar set the reader up for a variety of possible directions for the plot to go. Is there an assassin two tables over who can solve all of the MC’s problems - maybe out of generosity.

If you want to drop a hint, you could have a barfly mention he had just watched a marathon of Twilight Zone or saw a Night Gallery episode on YouTube. Maybe the bar has photos of old TV personalities including Rod Serling.

Maybe the more interesting question is, does your MC remember the night of the murders? Did he do it?

Your MC wakes up in prison - last thing he remembers is that last drink he ordered from Nick. Or is it? Perhaps he starts to tremble as memories flood him that he hadn’t lived - or thought so. Alternate life with Abby was hell and driven to desperation he murdered them all. Or, comes home from the bar and finds them all dead - minutes before the police arrive.

The bartender being named Nick is a hint, but you might need to play with it a little to make him less some random guy named Nicholas and more something very strange about this man whoever he is. A few lines of dialogue could accomplish this.

The tv show American Gothic created a town sheriff who turned out to be a supernatural force and, while not exactly the villain as his mission was keeping the peace in his town and protecting his people, he still came off like Satan’s second cousin.

I prefer stories where the hints are light and realized later - being spoon fed tends to annoy me. Be subtle with your hints and have some faith in the intelligence of the reader.

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If the majority of readers don't get it, the dots are too far apart.
Writing is like humor, in this respect. If the majority of your audience doesn't laugh at your jokes, then you aren't funny.
Fiction is like humor in another respect: It is entertainment, and for entertainment to be "good" it cannot leave people confused and not understanding what was supposed to have just happened. They will go along with you for about 15% of the story, all (adult) readers know this is part of the deal and part of the fun: You get dropped into strange environment with unknown characters and have to get to know them. But the unknowns need to be clearing away, they expect that too. Nobody is going to read 50 pages if understanding is not trickling in as they go.
I think you need to be more explicit; your clues are too obscure. Your objective is to entertain, not confuse.
Another way to accomplish what you want is a twist. Readers can be satisfied (not confused) by being tricked into believing the wrong thing, as long as when the big reveal comes around (Nick is really Satan!) this reveal is consistent with everything that went before; and they can see that Nick being Satan was just as viable an explanation all along.
To me, the best twist ever is in The Sixth Sense, the clues of what is really going on are scattered throughout, from the beginning. They are on display, but the writing expertly distracts us from them by always making something else more important to focus on, when they are shown. So they slip by, on the first viewing, but are clearly all there on the second viewing.
You can do something similar, prove Nick has magical powers, but he blows them off as a magic trick; a little hobby he has, messing with people's minds. Same thing with mind-reading, guessing the names of the guy's wife and kids, a mentalist stage trick. And of course, a magician never reveals his secrets.
You need more clues. It is a narrow path you have to walk. On the right side of the path, with lots of clues, there are no surprises or unexpected developments, so the reader gets bored. The story is too predictable.
On the left side, there are not enough clues or resolutions. Too many surprises, too many unexpected developments. You are demanding too much attention and memorization from the reader, forcing them to mentally work at understanding, and that is not entertaining. So the reader gets frustrated, the story is too difficult -- Too unpredictable.
I think you are off on this left side, you need to add enough clues as to what is going on to keep the reader engaged, but still not knowing quite enough so they are still wondering how it will turn out.

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When you're writing a story, you know all the clues and all the connections. Since you know them already, they might well seem obvious to you.

Are they as obvious to the reader? A good way to find out is to offer the story to beta readers, and hear what they say. If most beta readers get it, but one doesn't, you're probably safe. If most do not get it, they can't all be stupid and inattentive, right? So the fault might lie with you.

In particular, I would pay attention to beta readers from different demographics. It might be that a hint that seems obvious to you, is only familiar to people of your age, or your background. Remember also that some of your readers might only speak English as a second language, in which case knowing that "old Nick" is Satan might be more of a challenge. Especially if a person is also not a Westerner.

Now, explaining the story can feel detrimental to the story, like explaining a joke. It would also not be particularly interesting to those readers who got it without need for further explanation. The solution I would suggest is adding more hints throughout the story. Then, a reader can still figure it out, even if they've missed some of the hints.

Of course, giving the solution to the mystery, so to speak, isn't always a bad thing. In more than one story, understanding how a negative effect came to pass is necessary to negate it. In such stories, the act of restoring a "good" situation is cathartic, and built around the characters finally understanding what's going on. The readers who got it can pet themselves on the back, and enjoy the way the plot progresses from the realisation onwards. The readers who didn't, now finally get an explanation and can backtrack to find the hints at their leisure.

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What you can or should do depends on your aims. For example, do you want the ending to be ambiguous, obvious, or what I'll call Twilight Zone-y? By that I mean, "well, there's only one explanation, but it does require magic", like him ending up in a reality where he did marry someone else. Whichever one you want is fine, as long as you achieve it.

The problem, of course, is that there's always another off-the-wall option your readers hopefully won't think of. For example, maybe he never married Amanda in the first place, but due to some mind-bending he got the details wrong early on. While a reasonable reader will disregard that option as long as you don't give them reason to doubt the original narrative, the "number of explanations" is determined by what real readers are like, not just your words. You have to be very careful to write around that.

I know from experience watching TV or film with people of low or average intelligence that endings I think couldn't be clearer often aren't. In theory we can blame the writer instead of the reader (although I don't feel from the examples that come to mind like I know how the writer could have prevented the confusion), but I think the most viable strategy is not to worry about it too much as you write. Do your best to deliberately have your intended effect as you draft, but then see whether beta readers "get it".

The best stories have details that are realised on a second run to be foreshadowing. You may find it easier to add these in a later draft.

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This is easy to follow as an outline, because all the pieces are right there in one paragraph. It's impossible to say how it would read as a complete story. That said, here is some general advice:

In general (unless you're specifically working in a genre where the story is just an excuse for a puzzle that the reader will expect to have to work out) make sure your story will be strong on its own, even for a reader who never figures out the puzzle.
Play fair: If you want the reader to be able to figure out the puzzle, give them all the necessary information, don't hide things just to hide them.
Give them a reason to care. Assuming your story is more than just a puzzle, and the story elements are strong, the puzzle elements should relate to the story. For example, in the Sixth Sense the clues are subtle, but the twist relates directly to the main themes of the story. That way, when the twist is revealed it feels substantial, not just like a cheat.

In this specific case the dots aren't actually all that separated. It sounds like he finds out he's in jail for killing Abigail not long after the conversation with the mysterious bartender. That's not much of a stretch for the reader to figure out (particularly if they have any familiarity at all with speculative fiction). Then, they'll be waiting to hear what happened to Amanda the rest of the story, so they'll recognize her name when they hear it again. Someone who can't connect those dots probably isn't your target reader.

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If the reader isn't satisfied then that's no good. Teasing them a bit is OK provided you let them see the light at the end of the tunnel. Challenging them to a puzzle when they wanted a relaxing read is unsatisfying. Not giving the answer is definitely not on.

In my experience of reading draft pieces in writing groups, it's very easy for readers to lose essentials about the plot even when there isn't meant to be a mystery.

From your description I'm guessing that there's a short coda in the cell. I wouldn't be happy with that unless I'd had some clear hints that your character was unstable. Something that happens out of the blue as a fait accompli is telling when you should be showing. (A variation of 'it was all a dream' trope.)

You've got a difficult job making us care about an anti-hero. Why should I care what happens to a boring drunk? (That's not a criticism but a red warning flag that goes with the territory.)

It's always a problem judging how much hand-holding readers need. A little bit extra is unlikely to spoil it for the quicker ones. You don't have to be either arch or blunt. For example you can show us Fred is wealthy without him arriving in a Rolls Royce by other little details. Perhaps he shows photos of his latest luxury holiday. Job done naturally. You might add "I bet that was expensive Fred" and how he replies tells us about Fred's attitude to money. Two for the price of one!

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