ORLANDO, Fla. -- Are the Chicago Cubs at a crossroads?

Not exactly. Not after making it to the postseason three consecutive years with a young core that should still be getting better. But they’ve also stated that they want to make the postseason about seven times over the next 10 years, which means potentially not making it to October a few times. Could 2018 be one of those seasons? It’s possible simply because of the challenges at hand.

The front office knows this and admits to having specific work to do this offseason. They’ve known that work was coming for several years.

“I think fans should be extremely optimistic about this seven-year run that we’re hopefully on, and by no means do we look at it as a run of three years of contention and any sort of falloff,” Cubs president of baseball operations Theo Epstein said as the general managers meetings began Monday at the lavish Waldorf Astoria in Orlando. “But within any run of length, there are going to be years that pose more challenges than other years. We’ve known for a long time that 2018 was going to pose unique challenges because it was the year Jake [Arrieta] was eligible for free agency. It was also the same year a lot of our best players would enter the arbitration process.”

It’s the year John Lackey became a free agent, creating a second hole in the starting rotation. That’s the Cubs’ No. 1 focus this winter. Not far behind is a bullpen that needs some work, potentially including a new closer.

All teams, every year, have holes to fill. The Cubs have extremely important ones to fill in order to contend again. They’re not filling out roster spots Nos. 24 and 25 -- more like Nos. 4 and 5. That’s if you consider starting pitching the most important part of a baseball team. On top of it, the Cubs have their eyes on the free-agent class of next offseason, which includes sluggers Bryce Harper and Manny Machado, among others.

The Cubs have been clear about one thing in multiple interviews since the season ended: They will be cautious with their dollars while keeping future seasons in mind.

“I think there is a danger in simply being completely focused on building the best team for Opening Day,” general manager Jed Hoyer said on ESPN 1000 last week. “I think you have to look at it over multiple years and look at what players are available now [and] what players are available going forward.”

With that backdrop, the Cubs’ offseason begins. We’ll begin with their most important need. Filling out the starting staff will go a long way toward making the Cubs serious contenders in 2018.

Starting pitching

The Cubs made their big trade for a starting pitcher, getting Jose Quintana from the White Sox, last season. It’s simply not likely that they’ll find a match again, though it’s very likely that they’ll be on the phones trying all winter.

Even though they might not break the bank, the Cubs will be players for free-agent pitchers, including one of their own, Arrieta. There has been no momentum for an Arrieta reunion so far, but he’s likely to circle back to the Cubs after receiving offers elsewhere. Assuming he gets max dollars from another team, Arrieta is likely gone. He has shown no willingness to give the Cubs a hometown discount.

Meanwhile, the front office is casting a wide net, with Rays righty Alex Cobb in their sights. According to a source familiar with the situation, they reached out to Cobb early in the free-agent process, as he checks a lot of boxes. He’s a couple of years removed from an arm injury, has good stuff, would be making the move from the American League to the pitcher-hitting National League and gets an A+ in terms of fitting into the Cubs' clubhouse. Don’t dismiss that last notion. The Cubs are very mindful of whom they let into their club -- especially on a multiyear, big-money deal.

If they sign a pitcher such as Cobb, they can fill out the last rotation spot with anyone from a reclamation project such as former Red Sox hurler Clay Buchholz to a returning pitcher from Japan such as Miles Mikolas to perhaps Lackey if he indeed is not retiring. As stated previously, there’s a wide net.

The bullpen

Unlike last offseason, when the Cubs had no intention of re-signing Aroldis Chapman, closer Wade Davis still could be in the mix for a return engagement.

“Not only did he have an outstanding year, he was a terrific leader in the bullpen,” Epstein said.

Last year there was a run on closers. That might not be the case this winter, as many -- but not all -- of the potential contending teams have their ninth-inning guys. Perhaps unlike with Arrieta, it’s possible that the low-key Davis is willing to compromise to stay in Chicago. Perhaps a three-year, $50 million-$55 million deal could get it done.

“He knows that we don’t typically give long, multiyear deals to relievers, but it’s definitely worth talking,” Epstein said.

While admitting that the position is important, Epstein didn’t appear overly concerned with finding a closer, internally or externally. The Cubs feel that one will emerge if it isn't an obvious choice.

Middle relief also is an issue after the Cubs imploded in the playoffs. There are some decent lefties on the market, including former closer Tony Watson, as well as Mike Minor, who had a big year for Kansas City (2.62 ERA, 10.3 K/9). Minor could be on the Cubs’ radar as this year’s version of Brett Cecil, who earned a big contract (for seven years and $30.5 million) from the Cardinals last winter.

The team also is going into 2018 thinking that Justin Wilson will return to form after struggling down the stretch.

“We go in expecting him to pitch at a really high level,” Epstein said. “I fully expect him to go back to being a really effective relief pitcher.”

Trades

The Cubs are on record saying they might have to trade from their big league club to acquire pitching. It’s not likely to happen for a top arm, like it did last season, when the Cubs traded with Kansas City for one year of control of Davis in exchange for multiple years of control with Jorge Soler.

“You don’t want to make it a habit to give up five, six years of control for one year back,” Epstein said.

Incidentally, several general managers admitted the obvious on Monday: Kyle Schwarber’s trade value isn’t very high. Plus, the Cubs like him too much to give him away for some middle reliever. There are early indications that Schwarber is on a mission this offseason to return to elite form at the plate. The Cubs are likely to let him see that through.

Ian Happ probably isn’t enough to get a top arm, which means that Addison Russell or Javier Baez would have to be on the move to acquire one. That isn't likely to happen. Dealing either would turn a Cubs strength into a weakness.

Interestingly, six executives were polled on which of the two players has higher trade value. Three said Russell because he was more established, but two said Baez “by a hair” because of his high ceiling. One liked them both so much that he said, “Tell Theo or Jed to call. I’ll take either.”

The offense

Here’s where the Cubs might spend the least amount of time and energy this winter. They already made their big move on offense this offseason, replacing hitting coach John Mallee with Chili Davis. You might not think that’s much of a headline, but it’s clear that Mallee would still be with the Cubs if Davis hadn’t been available. That’s how much the Cubs think of the former 19-year player.

“His particular approach is really effective at increasing quality, situational [hitting], quality two-strike approach,” Epstein said. “A lot of these guys already have power. We need to continue to emphasize the areas where we can get better.”

The Cubs could kick the tires on a free agent such as Lorenzo Cain, but expect them to keep believing in their own on offense and allocating resources elsewhere.

The window for contention

Even without knowing who will pitch Games 4 and 5 next season, the Cubs have a good team. It became obvious as they were selecting hitters high in the draft that if they were to contend for several years, it would be with several different looks on the mound. This is one of those turnover years, but at least the Cubs have three solid arms in Jon Lester, Kyle Hendricks and Quintana. Filling out the rest of the staff will go a long way toward keeping the window to win open as wide and as long as possible.

“Right now the exercise is, how do we maximize the next four years and make sure you have as many bites at the apple?” Epstein said.