I would recommend going with the release order. The original is a self contained film made before it was known that the full trilogy would be made so it doesn’t leave open questions. Then if you enjoy it move on to episodes 5 and 6 before going back to 1-3.
However, having said that I once lent the DVD set of 1-6 to a friend who had never seen them without realising that he knew literally nothing about the films and he watched them in that order, telling me that this resulted in a massive shock part way through episode 3. If you do choose this order then you might want to add in Rogue One between episodes 3 and 4.
I watch 1-6 at least once a year and I believe that watching in release order is the best way. So start with IV-V-VI (the original trilogy) and then move on to I-II-III (the prequal trilogy).
Do whatever you want with Disney Star Wars. In my mind they are just fan fiction (a really big budget fan fiction). Solo takes place a little before episode IV. Rogue One leads right into episode IV. And of course 7-8-9 (the Disney Sequel trilogy) take place about 40 years after episode VI.
Go dig a hole in your yard and then do the following:
Watch Star Wars 1 (The Phantom Menace)
Watch Star Wars 2 (Attack of the Clones)
Watch Star Wars 3 (Revenge of the Sith)
Watch Roque One (Really very good if you can get past the mild push for diversity.)
Watch Solo (It won’t kill you.)
Watch Star Wars 4 (A New Hope)
Watch Star Wars 5 (Empire Strikes Back)
Watch Star Wars 6 (Return of the Jedi)
Gather up The Force Awakens, The Last Jedi, and The Rise of Skywalker. Walk into your backyard. Throw them in the hole. Pour gasoline on them. Burn them to Kingdom come. Then bury the ashes. Stomp on the ashes you just buried. Consider yourself lucky you never watched the movies.
The more I think about it. I would watch the originals first (4,5,6). Then watch Rogue 1. Then watch the prequels (1,2,3).
Then go dig that hole in your yard.
Gather up The Force Awakens, The Last Jedi, and The Rise of Skywalker. Walk to your backyard. Throw them in the hole. Pour gasoline on them. Burn them to Kingdom come. Then bury the ashes. Stomp on the ashes you just buried. Consider yourself lucky you never watched the movies. Join the fandom menace and do nothing but bash Disney Star Wars for the rest of your life for destroying a huge part of America.
Ive taken to watching the films in a different order.
Star wars, Empire, Phantom, Clones, Revenge, and Jedi last.
Treat the prequels as Luke really digging into the past and learning everything that happened in the 1 – 3 series then using that information to make the choice he made in Jedi.
Nothing the rat has created is worth the time or money expended to get them. If you insist on watching them 3.75 leads into Star Wars but really fucks up the first line Leia says to Vader. Its like they couldnt think past the ‘Can we do this’ stage to the ‘Should we do this stage’ and what does it change. 7 – 9 are still worthless no matter what happens they invalidate the entire true franchise.
Ever since Rogue One came out I like to think of Leia lying to Vader about the “consular ship on a diplomatic mission” as a last ditch, albeit lazy, effort to try maintain innocence despite Vader knowing full-well that she’s so full of shit there’s a brown spot on her white dress. It makes it easier for me to over-look that small detail mishap.
Other than that, though, I like your reasoning for why you watch the movies in that order. Maybe in the year between Empire & Jedi he asks R2, who’s never had a memory wipe, to show him all he knows about Anakin.
For the very first time watching any of them, go with production order. That way you don’t miss out on any of the original surprises. Once You’ve watched the original trilogy and then the prequel, in production order, any subsequent viewings can be done in chronological order. Adding in Rogue One between episodes 3 and 4 is not a bad idea, but frankly I would not recommend episodes 7, 8 and 9.