Sarah needs to have been dollified (meaning you've turned her into a doll through the Stone Skin spell (evidenced by the presence of doll joints on her arms in her portrait)), and must also *not* be a slave. At that point, after getting to the "you can have Val bimbo one person at a time" state of Bimbos Gone Wild, you'll see Sarah's icon in the school hallway, and then after talking to her there, you can find her in your bedroom so long as she remains not your slave, where you can bimbo her (the only case where Doll Sarah's portrait will change at all from personality alterations, as no other personality has an alternate version for Doll Sarah).
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Once you've gotten to the point where Val can bimbofy up to one other character at a time at your discretion as described before, then each character that can be bimbo'd at your discretion will show up whereever it is they show up, so long as there is no one currently in bimbo state due to Val. Kate shows up in the streets just outside of your house (the screen where you can transition to either your living room, the item store, the bounty store ran by Eric and Erin, the screen of the area just outside of the school, or the screen of the area just outside of the Enchantment shop). Once you click on her portrait there, and agree to let Val bimbo her, she should show up in your bedroom right away, and only go back to her spot on the street if you unbimbo her.
Teachers don't count as slaves you can give up to Cass, but do count towards the 3 you need for the first scene after giving up Sarah or helping Cass enslave her (depending on if doing the Rosa route or the Dan route). Only other students, and the non-Adult NPCs, count as ones you can give up to Cass.
Also if you get Cass to Level 20 before having gotten 3 slaves of your own after having given up Sarah, you'll get a trio of extra scenes where Cass laments how boring it is only having you and Sarah as slaves, and if playing as Dan, leads to a way to swap to being Rosa.
Enslave Val, and put her in Bimbo personality.
Periodically as you are levelling her and yourself up to Level 14, Mrs. Rack will have conversations. In the first one, lie to her.
In the second one, use the flirt spell, and then use boost on her after picking an option of which part of her body to try and pleasure. In the second to last one, offer to fix Mrs. Rack (DO NOT ENSLAVE HER, ENSLAVING HER WILL HARD END THE ROUTE). Then after fixing her, go back to your room, put Val back into Bimbo personality, and then return to Mrs. Rack. This will set you onto the NG+ triggering scene for the Bimbo World route.
There is then a subplot in the Bimbo World NG+ called Bimbos Gone Wild, which requires you to repeat the process done in NG, but at the point where Val is about to bimbofy Rack for you for the first time, try to intervene. That will then start Bimbos Gone Wild, which has you going around town starting in the streets outside your house and seeing Val slowly bimbofy everyone, when she does Molly in the shop make sure to go back in after the scene and chat with Molly, before heading towards the school, and to follow Molly's advice she gives in that talk with her after the scene where Val bimbos her.
You need to have enslaved Sarah for Cass, either by dating Sarah as Dan and then getting a scene where Sarah confronts you in the streets about Cass's control over you and choosing to side with your mistress, or enslaving her as Rosa, putting her in Mindless personality, and doing the Library play with scene with Sarah, then have 3 or more slaves of your own, for Val to not be one of those 3, have had the prompt to give up one of your slaves, have given up one of those slaves, and then getting Cass to ~level 20 and encountering a scene in your bedroom.
The chests in the Dungeon require specific gamestates, and the relevant characters in the active party. The first one you can see requires Sarah to be Dollified (and thus having Dollified Sarah in the active party when you walk up to it), the second requires a choice of either making Cassandra into a willing slave or becoming her sub (and thus requires having Cassandra in your active party when you walk up to it), the third requires Ashley to be cured of her "missing her soul disease" (and thus requires Cured Ashley to be in the active party when you walk up to it), and the fourth requires Kate (Rescue Girl) to simply be in the party (no specific gamestate beyond that, though the scenes tied to the thing you get out of the chest will require Kate to be in her Normal Personality, if she was recruited via taking control of her mind).
Trust is the Blue Bubbles, yes. Honestly, the easiest way to raise characters' Trust is to just grind up a shit ton of gems, and then repeatedly buy the +Trust item in the shop. There's no way to track trust like there is the Affection (how filled in the Heart icon is is the tracker for affection, but just giving 5 of the +Trust item to each party member who is proving annoying under AI control should be enough to get them all under manual direction.)
See title. No matter which routing I use to recruit Cassandra in a role that isn't as my character's mistress, she won't show up in the Party list after the fight with her. She only shows up on the active selected party slots if she forces herself in there via the Submissive Route where I intentionally make myself lose to her in the fight.
If you gave Val permission to bimbo others with your supervision, then all you have to do is have Val in Bimbo Personality, and no one else who Val can bimbo currently in Bimbo personality (so if your problem is that Julia's still in Bimbo personality, change her back), and go find a screen around the town that isn't the bedroom where a Portrait appears in the top left. Each person she can Bimbo is bimbo'd on a different screen, by clicking the Portrait. Molly is bimbo'd in the store, Kate on the streets (even if you've never met her before), Sarah via having her as not a slave talking to her in the School Hallway and then going to your bedroom and clicking her icon there (the reason why she needs to not be a slave. Being a slave overrides her bedroom icon for the bimboing with her slave talk dialogue), Cassandra in the school Hallway, Brittany in the Enchantment shop she runs, Dr. Tiff in her classroom/office, Ashley in your living room after you've cured her, and so on (go whereever you expect them to be that isn't your bedroom, for all the non-Sarah ones)