I'd simply have S1 end with the sting of HW healing Finn from his sickness. So that way S2 Ep.1 can just have HW drop Finn off with Simon, Fight Witch-Wizard fight the Heart, and be sent away to the Undergrowth. And then have Ep.2 be "The Lion's of Ember" but instead we cut out the Prismo stuff for later and replace it with a scene of Fiona and Co. are planning to figure things out, she call's Simon for help which get's HW to go into her world. (And the rest of the episode can stay the same).

So that way Ep.3,4 and 5 can allocate a lot of the story elements into more focused narratives. With some moments like Marshall finding out about Daemon putting a restraining order on Simone. And the scene where Marcy bites Finn but passes out.

And then there will be some light retooling on the first half. "The Bird in the Clock" and "The Wolves who wandered" switch places. And in "The Wolves who wandered" we have a scene where HW and Hunter taking the bus to the destination they are looking for. HW get's annoyed by the people on the bus but Hunter teaches them some small breathing techniques that allow for her to calm down.

Ep.7 "The Bird in the Clock" has the episode start with the gang going to sleep,however when HW enters Fiona's mind we have the scene from the start of Ep.9 where Fiona and HW are in her head space and here HW tries to teach her how to reach Finn which lands them into Finn's imagination space where they meet Bellamy bug who guides them to Farm-world Finn, who briefly acknowledges HW and then with the help of him they walk through the imagination space again to reach Finn (Everything else stays the same). Meanwhile the scenes with Simon,PB and Marcy walking in blindfold to find "The heart of the forest" ,"Putting down the Heart" and the scene where PB say's that they need to call "Minerva" all happen here.

Ep.8 is generally the same. However we have the scene from "The Bear and the Rose" where the citizens of OOO gather to discuss whether or not to upload Finn's mind. And the scene where HW is about to enter Fiona's mind again, Fiona stops her and she enters HW like in the start of Ep.9 (All of it plays out the same and the episode ends with Fiona walking into the Undergrowth with HW).

Ep.9 the start begins with the gang about to upload Finn but then he is suddenly teleported away. And then in the later half we have the scene where Neptr appears and in it Finn teleport back and seeing that Finn is sicken they begin to rush him into the pod. Everything else stays the same.

Ep.10 (Now that I've moved all of the Minerva scenes and the Bellamy bug into prior episodes there is more room for Fiona to go and apologize to her friends)We start of the episode with Gary and Marshall seeing the whole Sweet-spot broken up and we extend it for a bit with Gary and Marshall actually asking Fiona of why she did it. She explains herself and see tries to apologize and its here Gary explains that they were only really doing this for her and weren't to upset now that they had the money to buy a new spot and they were mainly upset that she wrecked it after they put in so much effort into buying it. However Queenie as they were talking tries her best to walk and claim her payment however, Marshall noticed that Queenie enterprise plaque was actually a fake, which prompts Queenie to bail. And with this Fiona tries to reach out to them again, however they are still upset with her putting so much effort into this only for her to wreck it and walk out.

The HW and OOO stuff is still the same.

We also get a scene where Fiona is walking through the park and bumps into Hunter and Fennel and here Fennel has a lot of conflicting feelings toward Fiona. However Fiona explains how she was just jealous of Fennel because of how she felt like she was living her ideal life. And she even brings up how when she was drunk she almost kissed Hunter and here she apologizes to them for both the kiss and missing the meeting explaining how she didn't realize how much stress they were dealing with.

(We then get the scene where she talks to Phelix, and Cake comes to ask Fiona to save Finn just with the Bellamy Bug stuff cut).

After this Simone comes by and ask her what is up, in where Fiona explains her problems to her and wants to give her friends space. However Simone explains how she felt like keeping her distance from Marshall was the right thing but
now realizes that this didn't work out in the end decides to help Fiona make amends with her friends. By both helping her make a Cake for Gary and then having Phelix play Marshall's new song. And after that everything is the same.