Charming Family Head Cannons (ft. Ella's step family as well)
When Dizzy first started going to Auradon she was really excited to meet Chad! She had heard she had a step cousin in school but was worried he wouldn't consider her family so she makes a blue friendship bracelet as an olive branch and gifts it to him at one of his tourney games before he goes off to college and he immediately adopts as an honorary sister.(he looks after her with his life for the rest of the semester)
Chloe is constantly asking Dizzy for stories about the core 4 when they went to AP and before they left the Isle. Chad feels bad that Chloe never asks him anything about when he went to school with them but his most detailed stories revolve around him being kicked out of Carlos & Jay's dorm for using their 3D printer without permission.
Speaking of 3D printers Chad definitely used to beg Carlos to 3D print toys to send to Chloe while he was in school because he missed his baby sister And Chloe also hated not hated not having her brother around during the semester (such toys include, a Chloe action figure, and her first practice sword)
Chad asked Dizzy to add blue streaks in his hair for a family portrait hoping to surprise everyone and Chad ended up convincing her to dye a small streak as well because their family
Lady Tramain is pretty much reformed by the time her and Ella reunited but the two try to steer clear of each other for the most part, they'd only really spoken twice since. Once to finally apologize for what she put Ella through, and once to thank her for not taking their problems out on Dizzy and treating her as a part of her family despite everything
The Charmings never visit Ella's family because they want Ella to be the one that makes that first step to rekindling that relationship and only if she wants to.
While Lady Tremaine doesn't treat Dizzy as bad as she treated Ella she still doesn't show her affection much so when she was worried the Charmings contempt for her might was over to her daughter it came off more like banning Dizzy from getting to know them at all
Ella does regular welfare checks on Dizzy whenever she visits Chad and Chloe (checking for bruises, malnutrition, exhaustion, etc) Dizzy hates that it's needed but appreciates such open affection
Dizzy and Chloe definitely braid each others hair and talk about their rebel girlfriends at sleepovers together.
Chad and Dizzy would probably destroy the whole house and start seven different wars if Chloe took so much as a break to grab a water while they were hanging out (and probably have)