So the dialogue between the characters never felt like a Tartakovsky-thing. They talk like that to each other in AotC, the writing is meant to evoke that, but if it’s building towards Anakin getting knighted and being deemed ready for a Padawan, I just don’t like it. I’ll put together a sample.
The issue with Ventress in the movie and early TCW episodes is silly, cus there is a deleted scene in the movie where she acknowledges her and Anakin’s Yavin encounter, but then the Hidden Enemy episode (which was produced after) put in the Christophsis fight which happens before the huttlet stuff… and it was just dumb.

In the Hidden Enemy Ventress does just leave, but that’s because she has scenes in the movie that this episode acted as setup for.

Curious to see what the suggested episode order was!
So I don’t have a problem with the Ep1 stinger not getting fully developed immediately. After all, the opening stinger has the Darksaber, Death Watch, and Maul - the only one of those we don’t get in s1 is Maul, which is fine, imo. Atm it doesn’t bother me. It feels like we’re getting pay off on bits, which I like.
Regarding Bail, I like his inclusion and I think it does add to the episode. My only issue is a lack of response. Just a verbal response from Anakin as he “walks past” Bail would go a long way to making him feel like he’s actually there.
Regarding SoM and RotS. Only the first SoM episode could happen before RotS, the second one has Obi-Wan in it and watching it before hand would just be confusing. We can talk more about it when we get there, but I have some ideas.

EDIT:

Here’s my sample of four edited Obi-Ani scenes in Dark Force Rising:
https://vimeo.com/560526924
(pass: restuctured)

In the first I cut almost all of Obi-wan’s objection to appointing Anakin to oversee the space forces.
In the second I cut Obi-wan saying anything other than “May the force be with you.”
In the third I cut Obi-wan repeatedly ordering Anakin not to follow Ventress and Anakin cutting him off.
In the fourth I cut what I felt was the most egregious of of Obi-wan’s Lecture.

My reasoning:
In the first and second scene, by cutting Obi-wan’s interjection and his explanation to Anakin that it was about his “maturity”, it reads much more (thanks to hearing his thoughts as he watches the army board the ships) that he is concerned more generally about the whole idea of Jedi fighting in the war. In the fourth scene Obi-wan says his concern regarding Anakin is that the Sith seem interested in him. If his concern was about Anakin’s maturity as he says in the current version, then when he later tells Anakin that he’s not a little boy any more, one wonders why he says it. Was it because he complained about not being trusted? Was it because he flagrantly disobeyed orders? Was it because he defeated an assassin? By trimming Obi-wan’s doubts, and his outright dismissals, what we get to see is Obi-wan voicing some concerns to a young man who he trusts and sees great potential in. Then at the end when Obi-wan recomends him for promotion it feels genuine, like Anakin has really proven himself, not in spite of Obi-wan’s trust in him, but because of it.

Edit edit:

Here’s a my rough take on an alternate opening for DFR. I think keeping Yoda’s intro is great, this is afterall kinda a TV movie/first prequel episode. It is okay if it has some pieces we won’t see again. But I like it better with the TCW:R logo.

https://vimeo.com/560596675 (pass: restructured)

Edit again:

Here’s more episode thoughts!

S1E4 - The 501st Legion

I think the test they fail, where the squad’s names get mentioned and Shaak-ti lays out their issues, is a stronger opening than the scene with the Bounty Hunter dressing them down. Consider this adjustment to the scene order:
Failing the test through the two hunters talking about caring or not caring.
Then your current opening scene.
Then Hevy & 99.
Then the two clones speaking to Shaak-ti

This order has a stronger narrative flow imo, and helps make it clearer that that what they might consider a lesser assignment, Shaak-ti considers a way to help them.

At 29:19, after 99 is sad about Hevy’s loss, the camera is briefly on Echo and his mouth moves, yet he doesn’t say anything. Drew me out of it.

Again, nice aggregation. You kept the best parts of the three episodes, maintained a good pace. It was a nice watch.

S1E5 - Cloak of Deception

The opening text her confirms my thoughts regarding changing the order of eps 2 & 3. If the next two times we see Anakin after Malevolence he doesn’t have Ahsoka, cus he’s pursuing Grevious, then this opening text fully explains that, and there’s no weirdness.

When Ahsoka draws her saber on Ventress, we do see her mouth move, and I think maybe adding a VO of her saying “Assassin!” or something would be nice. It was just odd, imo. Then Ventress says “Skywalker isn’t here to save you now” which feels out of place, because we have not seen Ventress interact with Ahsoka prior to this episode, and here Luminara is in charge. It seems most likely that she would assume Luminara was Ahsoka’s master. If you could splice audio to have her say “There’s no one here to save you, child” or something like that, I think it would help.

Consider modifying Ahsoka’s rant about Ventress at 12:01-08. Ahsoka doesn’t have any idea what the “bog witch” is capable of either, she’s met her once. If you combine her lines here with what she’s saying at 12:21-25 (so combine these two sequences) you could produce something like “I know Luminara is a Jedi Master, but I can’t let her face that low-life alone.” It would fit better with the story we’re presenting here.

I do think Ventress’ arc works as is, by this episode she’s had a few failures that were very close to being successes, with only the second counting against her, it feels like a decent progression. So I’m curious what the suggested reordering would do for her.

S1E6 - Children of Night

Opening Text Suggestion:
Change “his master Obi-wan Kenobi, to Master Obi-wan Kenobi” at this point Ben isn’t Anakin’s master specifically, he is a Jedi Master and the wording here might confuse the issue a bit.

Change “But his master, Lord Sidious” to “Yet, his Master,”

Your aggregation and trimming of these episodes was fantastic.

The single trial with the Savage/Feral focus was great, kept things moving forward, while still showing Savage’s motivations.

Two things:

So I kinda want to see Ventress’ disgrace happen later in the season, or at least have space between her appearance in Cloak of Darkness and this episode. I guess lair of Grevious will go here once edited right?

I don’t know that this needed to be a single episode? Two episodes, with the first ending with Dooku congratulating Savage on his attack on the temple, and the second episode starting with the Delta squad cameo. That way the arc can be a bit more spread throughout the season and not just shoved into a single episode. The second episode could go right before the finale, that way the thread is more present in the viewers mind when it comes up again in S2.

Also, imo, too many arcs just aggregated into a single episode runs the risk of recreating the anthology feel.