Love reading all of this and looking forward to more. Here are some thoughts ...
As I have made clear, I've been a HUGE Star Wars fan since 1977, # of times I saw each of the 'main 9' in theaters:
- Star Wars: >12
- Empire: ~6ish
- Return of the Jedi: 3 or so.
- Phantom Menace: 1
- Attack of the Clones: 3 (including once in IMAX)
- Revenge of the Sith: 2
- The Force Awakens: 3
- Last Jedi: 2
- Rise of Skywalker: 1 (no longer likely to become 2)
Here is an assumption: any adult Star Wars fan over 40 prefers the Original Trilogy. It IS Star Wars to most of us, warts and all. Also, if you go back and view press coverage and reviews, it was viewed as 'pure escapism' - which goes with my basic feelings since the start.
Some Pros and Cons:
OT:
+ It IS Star Wars
+ Great characters
+ Solid mythology
+ OMG the music!
- Empire had some work to do to make it a 'real Trilogy' (same for Jedi)
- By RotJ the 'multi coincidence' plot structure was overdone.
-Wait - a *second* Death Star? Isn’t THAT original!
Prequels:
+ Each one better than the last
+ Incredible soundtracks across the board
+ Obi-Wan was better than in OT
+ Seeing the 'arrogance of the Jedi' just before the fall really worked
+ Anakin grew into the role by last movie
+ Revenge of Sith managed to be better than Return of the Jedi (IMO, of course)
- the horrific racial stereotypes of Phantom Menace
- Cringe-y dialog
-Phantom Menace too clearly aimed at selling stuff to kids
-Entire trilogy tries too hard to establish contextualized backstory for everything - much of it we just didn’t need to know.
Sequels
+Solid characters throughout
+Really good acting, great chemistry
+fun set-pieces, cool Jedi powers, excellent lightsaber battles
+In particular the post Snoke scene in TLJ is pretty awesome
+Enforces the failure and arrogance of the Jedi (TLJ-only)
+Many EU callbacks (Sun Crusher becomes Starkiller, Clone Palpatine, etc.)
-WTF happened to John Williams excellence? Soundtracks are a throwaway.
-Force Awakens destroys everything the OT accomplished
-Yay, another Death Star-ish thing (and yet another by RoS)
-TLJ relies on things (like fuel) that have never been brought up before
-In TLJ nobody trusts each other, even on the same side … and people alternate between clairvoyance and idiocy.
-RoS betrays everything good or bad about TLJ and uses so much time doing so it is unable to come up with a real sense of purpose
-RoS … ugh, so in the end of the ‘Skywalker Saga’ the climax is a battle between two Palpatines? Seriously?
-RoS engages in so much fan-service (Chewie gets a medal!) and ‘playing it safe’ (Rose Tico) that it drowns out any attempts to establish real empathy with the characters
-RoS feels like a ‘not bad’ Star Wars movie due almost entirely to Ridley & Driver … but once you have a chance to think about it … it gets worse by the hour.
-For every great new Force power revelation, there is another that is a McGuffin (heal is great when Rey uses it on Ben, but at the end is Rey actually dead or just near-death? Is it heal or resurrect?)
-So much of the Sequel Trilogy ends up as ‘cut rate rehash’ - remember discussions about ‘Dash Rendar’ from ‘Shadows of the Empire’ game being an EU Han Solo wannabe? Here we get Poe suddenly being a Han Solo rehash, cut-rate Tatooine (Jakku), cut rate Mos Eisley(where we see Maz), and on and on.
I really enjoyed Force Awakens even though I disliked much of what it did to the OT (and of course how it laid waste to the non-Canon EU). Rey is a classic character (any ‘Mary Sue’ assessment is misogynist BS) who has honed skills and is very strong with the Force. She is in line with folks like Luke or Anakin or Harry Potter - obviously over-powered for ‘plot reasons’, but not out of line with other ‘hero’ characters (other than being female, which explains ~100% of negativity). Other characters were interesting, and the interplay and chemistry actually worked.
The Last Jedi had some really interesting things, most for me was Luke’s arc … he is the embodiment of the PT hints at the failure of the Jedi through arrogance, something that Obi-Wan and Yoda each failed to fully grasp and failed to teach Luke. It took the near destruction AGAIN of everything to teach the lesson that Qui-Gon and Dooku and others were trying to show - that balance isn’t the absence or ignorance of one or the other.
Rise of Skywalker ... well, as you might have guessed, I was able to stick with things through the first two, and my pretty serious Star Wars Fanboy ‘rose colored glasses’ helped me through viewing RoS ... but since seeing it on opening night, every time I think about it, it gets worse and takes part of the Sequel trilogy with it.
Tl;dr with the passage of time the Prequels get better, whereas the Sequels get worse.