Two of my theories to explain away certain unanswered questions and one question I never see asked
Why did Chris drive away in his car instead of letting the counselors drive it to Harbinger Motel for the night? While this may seem like an obvious solution considering there's still several hours left until nightfall when he leaves them, I would say this: someone had to free Travis from his prison cell. It's not Bobby or Jedidiah as they are a constant presence in the early hours of the evening nor Constance as she's clearly been left out of the loop in regards to Travis' encarceration of Max and Laura. Chris must have been in such a rush because he felt that he must have a one on one conversation with Travis in person with enough time to make it back to the Hackett house. What that conversation might have been, who can say, but Chris is the only one who could have freed Travis.
What happened to Ann Radcliffe, the missing hiker? Ed Benson's body is found at the bottom of Lake Septimus, presumably swimming away from some threat only to get tangled and drown. Some theorize that Anne may have simply been killed and eaten, but to that, I say, who wrote down the criptic poem on the wall of Laura's cell? Doesn't seem like Travis would write it down himself nor anyone else associated with him as it paints him in a negative light. A quick google search of the name Anne Radcliffe comes up with an 18th century English novelist and poet that specialized in supernatural gothic fiction and was a highly influential contributor in the genre. I believe Anne didn't die the night she and Ed wandered into Hackett's Quarry, but rather survived and was apprehended by the Hackett's to prevent their family secrets from going public. True to her namesake, Anne Radcliffe might have been a poet who spent some time alone in Travis' cell, possibly going mad before meeting her ultimate fate.
Lastly, one question I never see asked but it eats at me: Why is Jedidiah messing with the trail cams as seen by Dylan in Chris' secret security room? I already know the real answer: to manufacture tension. Jed and Bobby's intentions are unclear to first time players and they're meant to be the most telegraphed red herrings of all time, but within the world itself, what possible motivation could Jedidiah have for deactivating the trail camera considering that his and Chris' goals are one in the same: to track, locate, and kill Sylas? This just always seemed counter productive to me.
Edit: Here's a third theory that I had also come up with but blanked out on while writing the post: the financial decline of the Hacketts. The Hacketts come from money being the descendants of a profitable quarry, there's evidence that they were once bootleggers, own a scrapyard and a summer camp, yet they live in squaller and the lodge is in need of upkeep that they can't afford. Interestingly enough, they seem to have gained a lot of insight into the werewolf curse over the last six years since Sylas first bit Caleb. Eliza would have been the only individual locally that could have answered any questions, but she's dead and her spirit hates the Hacketts, so they would have had to outsource for any and all information they've obtained. I believe they directed a lot of their resources and finances towards learning as much as they can about the curse to cure the afflicted members of their family and in implementing security measures such as the newly renovated security room, the electric cells under the Hackett house, and the stock piles of special ammunition they hoard. Their business ventures and living situation have all been negatively impacted as a result.