I fully expect Filoni to do something about Ahsoka and Sabine searching for Ezra around the same time as The Mandalorian (and I think it would rule if those characters showed up on Mando when that other hypothetical show/miniseries/movie/whatever gets going, a la that one TNG 2-parter where they went to DS9). As for whether or not Dave is a reasonable or probable pick to replace Kennedy at some point, I kind of feel like he’s too much of a writer for that gig. Does that sort of job typically go to a creative?
Yeah I’ve been waiting since Rebels ended for the announcement of a search for Ezra show. I hadn’t even considered the possibility of Rebels crossing over in live action on Mandalorian. That’d be cool, even if I doubt it. More likely we’d see background characters go back and forth, like Favreau’s new Paz Vizla character from TM. Either way if they do make that show there will have to be some element of crossover, at least insofar as how Mandalore and Mandalorians are treated, considering how big a storyline for Sabine that was towards the end of Rebels.
As for replacing Kennedy, it’s not necessarily a simple answer. It’s not atypical for the head of a production company to be a creative. A germane example would be George Lucas, obviously, but also someone like JJ Abrams and Bad Robot. Of course, Lucas is an example where running the company sort of pulled him away from the creative stuff more and more, and JJ seems to be a little similar where most of his output recently is producing work. But producing can be creative as well, and you can see something like Marvel Studios where Kevin Fiege is sort of the show runner of the MCU (as the producer of all of those movies), as well as the president of the company. That said, LFL is a little unique in that has a number of different facets (ILM, for instance), including future films that won’t be Star Wars (or Indy), in addition to the SW multimedia franchise.
I don’t know what role Filoni would take, were he to get a promotion, but one would think it would be some sort of overall position with a specifically creative bent, whatever title that would end up being (perhaps something like CCO, even if not president). Of course, this is all dependent on what he wants to do, but like I said my point is that he would seem an attractive candidate for such a thing.