I believe the Cubs organization is at a point where the FO can afford to be even more patient than normal, largely due to the strong farm system. This allows him more options and flexibility than usual in FA.
Jed doesn't NEED to sign a FA CF like Bellinger. He has Tauchman, Canario, and PCA if needed. He can also acquire a stopgap in a small trade if needed, or sign a guy like Bader until PCA is ready.
Jed doesn't NEED to sign a FA SP like Imanaga or Montgomery, in the short-term he can also trade prospects for a SP with 1 or 2 years of control left until Horton, Wicks, and Brown may all be ready to join Steele, Taillon, Assad, and Wesneski as rotation options.
He doesn't NEED to sign a FA 1B or DH. He also has Mervis, Morel, Canario, and Wisdom as options there, and can also make a trade for one.
Similar with Chapman. We have Morel + Madrigal + Wisdom, then Murray + Slaughter in AAA, plus Shaw in AA who might even be ready by the end of 2024 or next season. Plus trade options on the table too. If all those guys get the flu they have Triantos, Mastrobuoni, Strumpf, and Bote in the upper minors or on the bench as well as backups. We have a lots of depth this year as most positions.
I think Jed will use this flexibility to wait out the market and pluck the best value deals that present themselves when comparing all the options in FA and in the trade market. We can be sure he has done all his prep work with teams and agents and is simply waiting until the market presents the opportunity to pounce.
If a FO's job during the offseason is primarily to maximize the amount of talent and potential number of wins the team is likely to achieve given the payroll budget they're provided by ownership, in both the short and longterm, then this is a logical approach.
Jed's been working in the high levels of MLB front offices for 20 years for big market teams who have won a few World Series rings, so this isn't his first rodeo, so for now I trust he knows what he's doing.