CHICAGO -- The Cubs were counting on their collective postseason experience to carry them well into October. Even with the offensive issues that plagued this season, the team was optimistic that the postseason reset could provide a necessary mental lift.

After scoring just one run in the two-game sweep by the Marlins in the National League Wild Card Series, the Cubs are now forced to examine the path forward. The core of the roster provided a World Series in 2016 and multiple playoff berths, but the past few years have ended in disappointment.

"We have to be honest about our performance," Cubs president of baseball operations Theo Epstein said following his team's early October exit. "Is it possible to thread the needle and improve in 2021, while also setting ourselves up for the long-term future? I think it is.

"On one hand, we have to be honest about our performance. We have not gotten to the point with our offensive production that we expect it to get to, with a number of players who are really talented and have done some remarkable things in this game."

With that in mind, here are five questions facing the Cubs this offseason:

1. Is this Epstein's last year at the helm?
During his season-end Zoom discussion with reporters, Epstein expressed that he is expecting the "status quo" for the Cubs' leadership structure. That said, he added that there will also be a mindfulness about a potential transition process atop the front office for after the 2021 season.

Epstein's current five-year contract runs through 2021, and he intends on staying on as the president of baseball operations during that window. It is quite possible that general manager Jed Hoyer moves into the front office's top job for '22, and works with Epstein this season on preparing for that kind of transition.

"At some point, there's going to be a transition," Epstein said. "And what's next with the Cubs is more important than what may be next for me. But I'm invested in the Cubs. ... We're all focused on how to be successful in '21, and how to improve our postseason performance in '21, and how to build that long-term success."

2. Who will be retained from the core group?
The clock keeps ticking toward free agency for Javier Báez, Kris Bryant, Anthony Rizzo and Kyle Schwarber. With the Cubs picking up Rizzo's $16.5 million team option for 2021, all four players project to hit the open market in '22, barring any contract extensions.

Essentially, that means all four players would be on "one-year deals," which Epstein noted can be a valuable dynamic for planning. Landing impact players on a one-year deal could be attractive for other clubs via trade, or it could simply help the Cubs in their own planning for contending in 2021.

"That's a good position to be in," Epstein said.

All four players are coming off subpar offensive showings in 2020, so that does throw a wrinkle into the situation. Báez and Rizzo still look like the best bets for an extension, while Bryant and Schwarber might be more likely to be dangled in trade talks. Each of these fronts have unknowns that the Cubs need to sort through.

3. How can the offense be fixed?
First, let's start with a positive: The Cubs' top three position players in 2020 by Fangraphs' WAR (Ian Happ, 1.9; Jason Heyward, 1.8; and Willson Contreras, 1.6) still have multiple years of control. And overall, Chicago made plenty of hard contact as a team, ranking fourth in the NL in hard-hit rate (39.9 percent).

The issue for the Cubs was that Báez (57 wRC+), Bryant (76), Rizzo (103) and Schwarber (90) each had career-worst campaigns. That contributed to another season of subpar contact (72.8 percent, 14th in the NL) and a stunning lack of production on fastballs in the strike zone.

Part of the solution will undoubtedly be counting on positive regression over a longer season. Completely overhauling the lineup would be a tall task, especially for a team not entering a rebuild. The goal then should be to see what exists on the trade market, while identifying offensive characteristics in targets that can not only tighten things up in 2021, but help build a better lineup down the road.

4. Will Jon Lester be re-signed?
The Cubs declined Lester's $25 million option for 2021, but that still netted the veteran lefty a $10 million buyout. Lester has expressed a desire to find a way to stay with the Cubs, and everyone around the organization has immense respect for the pitcher. Bringing Lester back on a team-friendly deal is not out of the question by any means.

"He's made a huge impact on Chicago Cubs baseball," Epstein said. "And it remains to be seen what the future holds. He's someone I really admire and always will."

5. Is there enough rotation depth?
The Cubs will return in 2021 with two of the top 20 pitchers in terms of Fangraphs' WAR in Yu Darvish (3.0, second in MLB) and Kyle Hendricks (1.9, 18th). That is a great starting point. Behind them, Alec Mills has earned a spot and Epstein said that Adbert Alzolay is "primed" to slide into the rotation.

While Lester might still factor into the picture next season, the Cubs need to look for additional rotation depth. Maybe trading from the core, for example, can help net a controllable starting pitcher. Internally, top prospect Brailyn Marquez will also be knocking on the big league door in 2021.