I still think we're gonna sign a SS next year - assuming they aren't hedging towards a rebuild. Didi's defense is already declining, he's just better than Segura (or any other option the Phillies had once they decided against Simmons).
I also think that Stott is a non-factor. Many scouts don't see him sticking at SS, but regardless, he has yet to even play a game in High A. If he forces his way to the majors next year, that'd be great, it would mean he's a true top prospect, but more likely he's still adjusting to AAA next July.
You won't get anything in return for Segura because $7.5 million is still above market value for an 1.5-2.0 WAR 2B. But you still do the deal.
Kingery is a whole other set of question marks. He could end up staying in CF, he could continue to be a perfectly good super-utility value (even as his salary rises), he could play 2B, or we could be having this same conversation about him in 2023 (i.e., sunk cost, can we dump him?)
But either way I'm not worried about having a hole at 2B. It's easy to fill (unless you're dreaming of another Utley) we just keep doing it the hard/expensive way.
While Dombrowski has said the right things about not being overly aggressive/short-term, his history is his history, and I imagine that his apparent success with getting Middleton to raise the 2021 budget will be followed by more win-now moves over the next three years - so long as they are actually winning, that is.