Hypothesis Consistent with Fact?

How far, in your opinion, is Hypothesis Contrary to Fact always fallacious? I'm aware of mutual exclusivity being one of the exceptions, but put that aside for now.

Is it possible to, in good faith, speculate about the past/future with hypotheticals that are likely to hold true?

Example:

Enid misses her exit on the motorway and has to turn at the next opportunity, which is quite a distance away. By the time she's able to do so, she is behind schedule.

"Ugh," she groans. "If I hadn't missed my exit I'd have been on time for that damned appointment."

You, being the uber-logical, rationalist skeptic that you are, say "Hey! You're committing the fallacy of Hypothesis Contrary to Fact! That's invalid reasoning!"

Enid looks at you as if you are an idiot. "Of course it's valid reasoning," she snaps at you. "Do you know how long I had to drive to get to the next turning point? Before then I was only 5 minutes away from the clinic."

Now you could look at this and add a number of possibilities. There could be more traffic on the way to the clinic. The car could break down. Enid might have crashed. But it's at least just as speculative as her statement; probably more so. In addition she has good reason to believe what she's saying; missing your stop on the train or bus has a similar effect of slightly delaying your commute.

In short; the more immediate the connection between the events, the less fallacious in my opinion.

A fallacious example would be below, for comparison:

Fred sighed and glanced at his son Greg, who was tuning a second-hand guitar some distance away. "Man, if you'd simply stayed in college and graduated with a degree in finance, you'd be making a decent chunk of money right now. Instead you're wasting your time - and my money - on a failing music career, an utterly fleeting phase of your life."

"IT'S NOT A PHASE DAD!", yelled Greg, instinctively pulling one of the guitar strings back so hard he snapped it. Calming down, and with a sweep of his unkempt hair he added, "it's a lifestyle."

Aside from the father-son relationship being one uncomfortable convo away from snapping, not unlike the guitar string, Fred commits the counterfactual fallacy by failing to support his claim that Greg would be better off as a financier. Maybe he wouldn't have succeeded in getting a job. Perhaps he wasn't passionate. Maybe he'd have gotten depressed while in college and done...some...horrid stuff. In short, there's no clear path between the two like there was in Enid example, and so it's more fallacious.

None of these are listed as exceptions on the fallacy entry.

TL;DR - am I correct in stating that Hypothesis Contrary to Fact is less/more fallacious (perhaps totally or not at all) depending on the connectedness of the events, much like the Slippery Slope?