When the sun set on Boston's Fenway Park on Sept. 29, it brought with it a 5-4 defeat that, in many ways, typified the Orioles’ season. There were oddities and bullpen blunders, the occasional how-did-he-do-that defensive play and another lead that slipped away in the later innings.

Such was the case often in the first season under executive vice president and general manager Mike Elias and manager Brandon Hyde. When the dust settled, the Orioles went 54-108 in Year 1 of the new regime’s rebuild, which saw considerable progress on the farm system, sizable challenges at the big league level and change come to nearly every facet of the organization.

Though the O’s now head into the winter with far less uncertainty than they did a year ago, this offseason should be no less transformative. And with the World Series come and gone, it can now begin in earnest. Here are five questions the club must answer during it:

1. Given a full offseason, what moves does Elias make?
Everything was condensed last winter, with Elias landing the job in mid-November and Hyde coming onboard a month later. By that point, Elias and assistant GM Sig Mejdal had less than two months (including the Christmas week) to cobble together a coaching staff, assess the organizational landscape and get a grasp of what they were dealing with roster-wise before Spring Training opened.

That’s all different now. The Orioles spent 2019 churning the 40-man roster, getting nascent analytics and international scouting operations off the ground and making sweeping alterations to their baseball operations, amateur scouting and player development ranks. This winter will be more about hiring, providing Elias his first full-blown chance to shape the organization in his vision.

“I expect to backfill all those numbers, if not more,” Elias said recently. “It might not be the same title, location, whatever. We’re going to be growing as a department and in player development, specifically. I expect an increased head count relative to what was here, for sure, but we’ll be doing a lot of different stuff across all levels.”

2. So what does that transformation look like?
That remains to be seen, but the pieces are beginning to fall into place. Elias has added five new faces -- Mejdal, Hyde, newly-promoted director of pitching Chris Holt, international scouting director Koby Perez and director of player development Matt Blood -- to authority positions since taking over last November. He promoted Mike Snyder (pro scouting director), Brad Ciolek (domestic scouting supervisor), Kent Qualls (director Minor League operations), Kevin Buck (director baseball administration) and other holdovers this month, while parting ways with Brady Anderson and upwards of 30 others.

The question now is how much those departments swell and what shape they take in the months to come, particularly in the analytics, international and player development spaces. Elias has been vocal about his desire to catch up with the rest of the industry when it comes to technology; their recent partnership with 3D evaluation and biofeedback company K-Motion marked a step toward advancing those goals.

With Blood as the point man, the Orioles are looking for progressive, data-literate instructors to fill player development positions, some of which Elias said “never existed before with the Orioles.” They need to fill several vacancies in more traditional Minor League coaching positions, and they plan to add one additional development coach to each of their five top Minor League affiliates. Elias must also find replacements for Howie Clark, Arnie Beyeler and John Wasdin, after opting not to retain them as assistant hitting, first base/outfield and bullpen coach, respectively.

“We’ve got a lot to navigate between now and then, and these things take time to put together,” Elias said. “There will be a lot of hiring around here.”

3. Will the Orioles trade Mancini?
They’re likely to explore the possibility, but the chances feel more remote than they did two months ago. That said, Trey Mancini’s sensational September went a long way toward quelling doubts his 2019 breakout was for real; he emerged as the face of the franchise and one of the American League’s most productive hitters.

But nobody is untouchable at this point in a rebuild, and the Orioles are likely to shop Jonathan Villar and their other better chips heavily this winter. On paper, Mancini is their best trade bait: he’s 27, just entering his prime, and under club control through 2023. It’s unclear what his market would be given the deep pool of bat-first corner-outfield types set to hit free agency, but the Orioles aren’t going to put themselves in a position where they don’t find out.

4. Who to protect on the 40-man?
It was telling how when asked recently to name his winter priority roster-wise, Elias said choosing which prospects to protect from the Rule 5 Draft. Ryan Mountcastle, Dean Kremer, Keegan Akin and Cody Sedlock are locks; Ryan McKenna and Alex Wells will warrant closer consideration.

(Yusniel Díaz, Michael Baumann and Zac Lowther don’t need to be protected until next offseason.)

5. What to do with Davis?
The questions will hang over Chris Davis for as long as he’s tethered to the roster by his seven-year, $161 million contract, and they're heightened by the events of what was his third straight empty offensive season.

After slogging through a historically bad 2018, Davis hit .179 with a .601 OPS in 105 games in ‘19, endured an MLB-record hitless streak, got into a visible dugout altercation with Hyde and saw his role essentially vanish by September. That he plays the same position as the Orioles’ best player (Mancini) and most-ready prospect (Mountcastle) further clouds his future with the organization.

When asked recently, Elias was pointed in his remarks about Davis’ lack of production, but he reiterated that the veteran’s status hasn’t changed. He said he fully expects Davis to be with the team in Sarasota, Fla. next spring; what happens then remains unclear. For Davis, at least, the situation is tenuous enough for him to publicly ponder whether last year’s home finale was the last game he’d play at Oriole Park.