I think anyone recommending any of the live-action shows as a good starting point is wrong. I'm also incredibly biased, but episode 4, to me, is where every new fan should start. You're not going to find anything that defines what Star Wars is more than episode 4 and the rest of that trilogy. Skeleton Crew and early Mando are unique in that they do manage to tell a self-contained story on their own, but there are nonetheless aspects of those shows which require previous knowledge of the universe to fully appreciate, recognize, or understand.
I think the better way to put it is that most of the live-action shows are Star Wars shows based on Star Wars and don't function the best when viewed through a non-Star Wars lens. BOBF is carried by our knowledge of Boba Fett as a character. They do some interesting things with him, but I don't think we spend nearly enough time for someone new to the franchise to really develop that bond and care enough about what's going on. Ahsoka, as a show, you quite literally need to have background knowledge because they present us with a bunch of information that someone new isn't going to know anything about and will likely just be more confused than intrigued, I think.
Skeleton Crew is built as its own thing, its own world, and it actually is structured more like a standard, regular story anyone and everyone can relate to, regardless of experience within the franchise, in my opinion. Most of the seasons of live-action television we've gotten, I think, their strengths come from the way they continue the Star Wars narratives—how they handle the character work they do with characters we had already been exposed to in previous stories, stuff along those lines. Most of the time, I don't think the strength comes from the actual quality of the foundational, structural storytelling itself, if that makes sense.
To build upon this once more, I don't think I would've watched a show built like Book of Boba Fett—the same storytelling quality, same length, similar cast of characters—if it wasn't Star Wars. I don't think I'd like it if it wasn't Star Wars. The fact it's Star Wars and it has characters I'm familiar with, and I can make those ties to previous stories, seeing the way certain characters have grown or shrunk in their mental and physical capabilities, that's what makes me interested.
Skeleton Crew, on the other end, is the kind of show I could see myself watching because it's not as reliant upon trying to feel like Star Wars. It does feel like Star Wars, but it comes from what vibes as a natural, organic place, rather than trying to be it with cameos, Easter eggs, etc., that feel inserted more than genuinely needed. I'd love to see someone like Hondo, or Lando Calrissian, or Han Solo, Carson Teva, or Din Djarin (who are now characters we're more familiar with, though not to the level of those others) in Skeleton Crew, but the story doesn't need them. It'd be cool to see them, but the story is strong enough without them.
