How Many Screenshots Are Too Many

At what point am I offering too many screenshots? I am working a redesign of my company's help guides - these guides are mostly centered around our hosted mail services. How to set up Outlook, set up a smartphone, things of that nature. The basic problem I'm looking to solve:

"Develop a 'how to' guide that communicates a technical process clearly so that readers of any experience levels can follow and understand."

I've scratched together a very rough layout concept of the basic elements that may appear on a given page. A potential solution I see, is offering broader screenshots that capture multiple clicks in one image. But, I'm worried in my hope to make things simple I have instead made them confusing/distracting.

I'm staring at my wire-frame and the visual portion (granted, I used red ink) appears very demanding.