Yeah, I see your motivations behind all of these choices. I have also said in the past that if you’re gonna do the Machete Order, you might as well do ROTS as the only prequel flashback rather than 2 and 3. I do agree that maybe there are a little too many “flashbacks” that could make the watch through feel a little disorienting, but maybe you could show someone this order and report back to us. If you’re worried about overwhelming someone with too many movies and flashbacks, at the very least I think you could do IV-V-III-VI-VII-VIII-IX.
This makes sense to me.
Honestly it depends on the first time viewer. If it’s a kid, I wouldn’t dare risk not showing in release order. Yet, even if they’re older and know the twist, I probably wouldn’t risk not showing in release order because the PT could easily turn them off to the whole thing. In fact I’d only do chronological order if the first time viewer in question is fully committed to watching all of them, and then release order for someone who’s open to viewing all, but not sure. And then ^this order for someone who doesn’t really care about the prequels, so they just get a taste.