If I'm being honest, I wouldn't wish working on Star Wars on my worst enemy. It has to be one of the most difficult IPs to work with. If you can get even 70% of what you do right, you're a god.
I mean, first you have the fans passion around it. So many have grown up with Star Wars and rather than grow out of it like other things we enjoyed as kids, it's been awesome enough to last through our lives. So it's a deeply personal thing for a lot of people as it ties to their own lives and doesn't just feel like disposable content they consume for fun.
Now you take that passion and then think of how many different types of Star Wars fans we have. The IP has been around for over 40 years with many different eras and types of media. You can have people who grew up solely on the prequels who have now been fans for 20 years. That's 20 years to love something that many older fans didn't even like on release and may not consider "real Star Wars". Something created by the guy who created the OT! It's such a weird scenario. Then you have tv shows, books, comics, games, and other media over 40 years in both legends and new canon. Fans pick and choose what they consume and what they like or don't like. More than any other IP I can think of, Star Wars fans have their own personal canon, picking and choosing what they feel is correct and ignoring what they think isn't correct.
Which is totally fine to a degree. Everyone is free to like or dislike whatever they want. But that also means people are going to have vastly different opinions on everything. And the more people dismiss certain Star Wars media, it gets tougher and less likely they'll be pleased with future projects that consider them canon. It creates like a thousand different fan types you need to please (which is impossible). Even among like-minded groups (like this forum) there are extremely varied opinions.
I know people like Jon and Filoni are also trying to play as nice as possible with all different media and eras and push for ways to enhance or improve those stories. This also means they will consider all existing content part of the playground, which is going to displease some fans before they even start.
That's not to say they just get a pass for effort. They are going to try new things and not everything is going to work, even with good intentions. There will be stuff that is weird, bland, or even bad. But man, it's really all-or-nothing with a lot of Star Wars fans, and that's a bummer. If this series doesn't live up to expectations, Jon is going to become a villain very quickly and people will start to dismiss his future projects before they even begin. I mean, I struggle not to overreact to things as much as anyone, but I'm actively trying to stay positive, look at the bigger picture and contextualize this stuff so I can try to be open to enjoying more stuff.