Any and all help is appreciated!

I dont know about the chase but you could use shurado,sailor sakura and probably kimimaro

My suggestion as that you use "ghost kill" tactic.

Sakura-x-Hinata
x-x-x (empty)
Main-Shurado-(oboro clon)

Skills = Mistery: Sealing Jutsu. Attack: Feather Jutsu.

Just keep trying with Kakashi until you got something that you are comfortable with.
Use Gamachu as summon.

or

x-x-x
Sakura-main-Hinata
x-Shurado-x

Hope it helps, report back in any case.

Problem is my "ghost kill" tactic is only level 2

try using hinata,shurado,kankuro GNW and ninja cat for summon
hinata at center front, kankuro behind 1 circle of sakura, main and right corner and shurado in front of it.

use dragon flame and the sleep magic for atk and mystery, genjutsu mirror, oboro, and celestial for passive
that's my current lineup and still works well :)

you have sailor sakura but not tobi? :D