It's almost impossible to improve by 10-15 games (even though the Phillies under genius manager Gabe Kapler did it last season ) But you have to assume this was an 87-90 win team when healthy, and try to improve it by 5 or 6 games.
Cutch in CF is an option but I'm not sure it makes the team better. Also he's the short end of a platoon and that's not actually going to happen (unless he turns out to be cooked).
Honestly I also kind of think with Dickerson it's best to just be impressed with what he did and thank him for his service then hope he can do it again (let alone on a three-year deal). But that does change if you trade Haseley. Or if the market isn't there for him and he's willing to take a reduced deal/role. These things have a way of working out once the injuries hit.
Unless they can trade for or sign a viable CF option keeping Kingery there half of the time is probably the key to everything. Easier to find other IF options.
The whole Segura to 2B (or 3B) scenario would mean getting someone like Grigorious (could he bounce back?), Iglesias or hey, Freddy Galvis to play some SS.
I think it's going to be a deeply crazy off-season, just as busy as last year. Because if Kapler doesn't go Middleton isn't going to be timid, and Klentak's job will be on the line. And if Klentak and Kapler both go who knows what a new GM would do, especially if it's someone like Gillick or Dombrowski ("like," not those actual guys) with little reason to think more than three years ahead.