The Jed Hoyer offseason playbook of flexibility and hunting for good deals has been broadly successful. The problem is that flexibility needs to go two ways, you need flexibility on your roster in order to facilitate the flexibility with the market. Two years ago it worked out great where Jed had Boras cornered. Last year it kind of blew up in Jed's face. When he whiffed on Scott and Bregman there was nothing left on the market worth buying and he just had to eat ~$10M that probably could have done something fun in November or December.
As the roster gets better, the odds of a 23/24 style windfall go down and the odds of a 24/25 style kerfuffle go up. This roster currently has few holes: one or two (depending on the Shota situation) rotation spots, most of a bullpen, and one or two bench guys.
The top handful of free agent bats are good enough to force their way into our lineup, but that's it. So like maybe you can get a great deal in January, but if those available deals end up being for Josh Naylor, Gleyber Torres, and Trent Grisham it ends up being moot. On the SP front I know we had the Boras 4 situation, but generally great options don't just sit around forever. The one place where the team is thin enough to just add talent where you can and worry about the exact fit later? The bullpen.
I don't want Jed to go all Dombrowski and spend a quarter billion before Thanksgiving, but I need him to be less passive. Saving $9M on Kittredge can't be for some January mystery box. It needs to be earmarked for something. Maybe it's Keller like you write here, maybe it's the difference between the Michael King tier of FA SPs and the Dylan Cease tier. Upgrading a 92 win team has to be a different process than upgrading a 72 win team.