Slight change of plans - I had the opportunity to binge a lot more these last couple of days, so I decided to keep my ‘big picture’ hat on and review the season four and five content, plus some cut stuff, to continue to refine and plan for the whole.

We follow a season of shades of grey, temptation and compromise. Our third parties are on the rise. The Republic have successfully trained rebels on Onderon.

The theme of the season is “the Clone Wars challenge even the strongest wills”, as all our strong characters face their greatest struggles.

Currently I think season four is looking like this (note that episode names are their originals, not my final choices):

SHADES OF REASON, where, after coming together near the end of season three, Maul and Death Watch take Mandalore. This doesn’t feature our main characters but placed first in the season it serves to elevate the tension, and turn those two long-running plotlines into a major focus for the remainder of the show.
SLAVES OF KADAVO, which brings all our characters to Kadavo to traumatise the lot of them. Aesthetically, this is quite similar to Onderon, which is a shame, but after the opening focusing on Mauldalore, I think it’s right to start the season with all our main characters. And to give Kenobi a break until his next major trauma. I’ll pretty much skip the entire first episode, as that’s mainly action and exposition, and we’ll just dive into the slavery stuff quicker.
BOUNTY, where Ventress meets with a free Boba Fett, and he’s a little bitch, but she does the noble thing. This is quite a weak episode, I think, because it’s almost all action with low stakes. Boba’s really weak and it doesn’t set up his future strength nor the ‘noble code’ or ‘ruthless bounty hunter’ traits he ends up with, so I actually think it’s a net loss for him. And Ventress’ small bit of growth, whilst technically setting her up for the Fall of Ahsoka arc, is really light touch. I could almost get rid of this entirely.
YOUNGLINGS vs HONDO is also not super. Sure, it shows more of Ahsoka’s competence in training Younglings, but in a less dramatic way than her Trandoshan arc. The kids are fairly throwaway now they’re not getting their own spinoff. Grievous and Obi-Wan are OK, but I’d cut most of the space battle focus. I can tighten this one up, but it won’t be amazing. I’ll be cutting the first episode (where the younglings get their crystals) entirely, since it’s not a value add to our story. That’ll end up in the pool of ‘bonus episodes’ I produce later.
MORTIS, as I discussed above, I’ll try to make mainly visions, but again it’s not great. At least it shows our main characters, which kind of balances the season out, but I don’t think it’ll land too well. Either way, I definitely think that here is the best place to put it - as late as possible before everything goes to shit.
THE LAWLESS, where Obi-Wan and Satine’s arc concludes, and Maul’s dreams are destroyed by his master. Now we’re back in the real good shit. I think this works fine paced a few episodes after Shades of Reason.
(/8) AHSOKA’S FALL. This can play out as two episodes - one up to the point where Ahsoka goes on the run, and the second where she’s recaptured and put on trial. I did think I might split this one around probably The Lawless, just to let a bit more time pass, and to further balance the season, but I don’t think it’s necessary. Though I might take the very first scene, of Anakin and Ahsoka on Neimoidia before they get called back to the Jedi temple, and use that elsewhere if I need to beef up another episode. It’s a nice moment to show their relationship’s maturity, but not strictly necessary here.

The only real issues I have with this season are the string of three weaker episodes (Ventress & Boba, Younglings vs Hondo, and Mortis), and the fact that it’s quite light on Anakin and Ahsoka’s relationship before her fall. Ideally there’d be something in this period of time which shows off their strength together and really gives Ahsoka a period of doubt in the Jedi order, but I don’t think there’s anything that’d do that nicely that fits in this period of time.

(Likewise, I actually think that my season two suffers from this as well, not having enough of the main squad together, much Obi-Wan, or much Anakin/Ahsoka time in the middle, and there’s no great option there either.)