1) Rebels is starting in 10 days and it'll be over the beginning of March. We have Han Solo coming out this May, and then we don't have Episode 9 coming out until December 20, 2019. The comic stories are limping along. I'm not sure what's coming out novel-wise. So it appears we have somewhat of a Star Wars "drought" coming between June 2018 and December 2019. Is this good? Is this bad?
2) We have Rian Johnson doing his own trilogy. No release schedule, not filming currently, and he's still thinking about ideas according to an article from January 16th. So I'm guessing he's in the writing phase now, will start casting/auditioning/etc later this year and start filming next year for a May 2020 release date.
3) We have David Benioff and D.B. Weiss doing "a new series of Star Wars films." after GOT is over. GOT is rumored to air April 2019 according to Maisie Williams. So they probably won't start writing/thinking about ideas for their films until early-mid 2019. Will their first movie come out in 2020 as well? Maybe December 2020? Two Star Wars films a year from two different teams? Will they stagger the releases to allow the ILM team to do the post production special effects work or will they expand the team? Johnson 2020, 2022, 2024 -- Benioff/Weiss 2021, 2023, 2025?
Final questions and thoughts...
4) What's Filoni working on? [Probably a new show, but when in the timeline and with what characters is anyone's guess at this point.]
5) Do we really want an Obi-wan movie? [I don't. The comic stories involving him all take place on Tatooine and are not very exciting. Leave it as is. He's watching over Luke and doesn't leave the planet to go on an adventure that we need to see.]
6) Will we see Episode 10-12? [maybe in 2026, 2028, 2030]
Now that Disney has made their 4 billion back, it's experiment time. Kennedy likes working with Johnson so we'll see how that gamble pays off in the future. Whether you love, hate, or are indifferent to GOT, in my opinion, it's the best show on television when it's new and I think Benioff and Weiss have a lot of potential to bring us some good stories. Sure, they don't have Martin's source material, but they have the Lucasfilm Story Group and plenty of "Legends" material to cherry pick from and make their own. So in my opinion, this is "fun" time for Disney and when "fun" time is over, they'll go back to the core Skywalker trilogy if there are any Skywalkers left by the end of IX.