Segura is just a complicated case. If we're out of contention, you still have to decide whether you want to spend $10 million or so to get prospects for him, or $14 million to still have him on your team next year.
Now, if you're planning to sign a free agent SS and confident you can get one, that changes things a little bit. You could make Didi your 2B and also hope that Kingery's in the mix. Of course we also might not have a 3B.
I don't know that I'm confident Dombrowski will be any less of a fence-sitter than Klentak was, given the state of the team. They don't look good enough to win a championship but they also don't look bad enough to throw in the towel. If they reach the point where they are trading Cutch, Neris and Velasquez, you certainly have to consider trading Herrera, and if you can also offload one of Didi or Segura you probably should. But will they sell that aggressively? The idea of an unusual or creative deadline deal, with bigger names or money on both sides, is probably a fantasy
And then there's also the early trend of truly terrible attendance, and the labor stoppage X-factor. It will be another interesting off-season no matter how it goes.