CHICAGO -- Cubs fans are hoping for an offseason full of reports about impact free-agent pursuits and blockbuster trades. With a month left on this season's schedule, Chicago is getting a head start on more nuanced decision-making.

Jed Hoyer, the Cubs' president of baseball operations, has called it one of those "good problems" that a team encounters. Chicago currently has a long list of players -- including some high-profile prospects -- who will need to be placed on the 40-man roster this winter for Rule 5 Draft protection.

"We're trying to figure out our roster, which is a bit more complicated than usual," Hoyer said. "We have had a lot of discussions about the 40-man for the last few weeks, how we're going to play it."

In a 7-1 loss to the Reds on Wednesday night, Cubs rookie Javier Assad walked off the mound in the sixth inning to a warm response from the Wrigley Field crowd. The young righty pitched 5 1/3 innings and allowed a pair of solo home runs, plus two runs after his exit, in his latest audition outing for Chicago.

“I've felt really good at this level and with my teammates,” Assad said via team translator Will Nadal. “Just seeing all the experienced players that are here, players that have their own routine, I've been able to look at them, see what they do.”

The 25-year-old Assad earned his promotion to the Majors with a 2.66 ERA through the Double-A and Triple-A levels this year, but he also fell into this Cubs' crowded category. Assad would be eligible for the Rule 5 Draft (held on the final day of the Winter Meetings in December) if not on the 40-man roster.

Players first signed at age 18 must be added to 40-man rosters within five seasons or they become eligible to be drafted by other organizations through the Rule 5 process. Players signed at 19 years or older have to be protected within four seasons.

There will be some clear-cut roster additions from the eligible pool, which includes highly-touted prospects like Brennen Davis (No. 2 on Pipeline's Top 30 Cubs list), Kevin Alcantara (No. 3) and Ben Brown (No. 7), among others.

But the eligible list includes dozens of players, including other Top 30 prospects like Yohendrick Pinango (No. 18), Chase Strumpf (No. 25), Luis Devers (No. 26), Ryan Jensen (No. 28) and Kohl Franklin (No. 29).

Rotation prospects Hayden Wesneski (No. 12) and Caleb Kilian (No. 14) were going to be added over the offseason, playing a role in their respective promotions to the big leagues this year. Kilian debuted in June, while Wesneski enjoyed a brilliant debut on Tuesday night.

In a few of the roster-bubble cases, the Cubs are trying to gather some Major League data and feedback down the stretch to help their offseason decisions.

"There's really only one level to evaluate guys on, you know?" Cubs pitching coach Tommy Hottovy said. "I think we try to evaluate guys at certain lower levels and project, predict what they're going to do in the future. The only way to really know that is to get them here and to see it.

"You see how they handle the moment, see how they react, look in their eyes, get a feel for whether they can handle it every day at this level. And so, we get to be around them and talk to them, and see how they act off the field, see how they act with their teammates.

"All those little things, those intangible things that you just don't get to see unless you're with guys, I think are extremely valuable."

During the recent trip to Toronto -- where the Cubs had two roster spots available with Justin Steele and Adrian Sampson unable to travel across the border -- Chicago used the series to see pitchers Brendon Little and Jeremiah Estrada.

Estrada dominated across High-A, Double-A and Triple-A, striking out 78 in 48 1/3 innings and logging a 1.30 ERA in the process, and was likely going to be added as a September callup. The series north of the border allowed Chicago to get a jump on that process, though the righty has had mixed results through three outings (including yielding one of Aristides Aquino’s two homers on Wednesday).

"Clearly, we've never experienced that,” Hoyer said, "with kind of the idea of having a free look and being able to call guys up that weren't on the 40. It was nice to get a look at both guys, but it didn't change anything."

There are still 26 games for the Cubs to use down the stretch to gather more information to lay the foundation for this part of the offseason.

"When you have no real strong 40-man roster decisions or no difficult decisions, then that's a problem," Hoyer said. "We have a lot of really difficult ones now, or guys that I think are deserving."