Well.... I kinda found my personal new favorite companion group for the next anime. This group idea will never happen, but I think it would actually be an interesting idea to be shown for once. Well...at least for me it would be a good idea.
My new main characters would be Ash, Lillie and Olivia.
Ash would be kinda the same as he is in Sun and Moon, but will have some trades from his DP era. Meaning he will be very goofy, silly, contacting and a bit naive, but will be a good trainer and will have some conflicts with his team mates, his Pokémon and his new rivals. For Lillie he will act like a big brother towards her and tries to cheer her up when she always feels very down.
Lillie would the new female lead and will act as the brains of the team and will try to find a new goal in her life where she can use her knowledge for good. I really do not want to see her as a performer like May, Dawn and Serena and I also do not want to see becoming a specialist in a specific type. I really want to see something new with her. In my own head cannon she will act towards Ash like an older sister. Always try to find a clever way in helping him achieve his goals as a trainer.
Olivia will be some sort of a spiritual successor to Brock. She is also very smart, but more street smart and tries to solve problems more of an emotional level, rather than a logical level like Lillie would do. Olivia will also be some sort of a mentor for Ash and will have a weird older and younger siblings relationship with Ash and Lillie. She will also have a similar running gag like Brock had back than where she tries to find herself a boyfriend but every single time some weird slapstick situation happens before she even can talk to the handsome guy of her dreams.
This would be the first time, we would see this character dynamic in a show. A young naive boy, a clever bookworm girl and a middle aged woman can not take a break from all the slapstick that happens in her life.