I'm looking for a sleeve to slide into briefcase/backpack that will hold my iPad, with a hard clear back case, and the Smart Cover, plus a Keys to Go and the Apple Pencil.
I know that a user here - sparkomatic has the iPad Pro 9.7 and Keys to Go keyboard which he fit into a Waterfield sleeve and also a Pack and Smooch sleeve. Both are pricey but very good quality. I had the Waterfield sleeve and it easily fit my iPad Pro 9.7 with silicone case and ASK. The Keys to Go is really thin, so it wouldn't be an issue. Links below.