I don't know why you found it difficult. There are many ways to do this but I'll only show one. I just tested this and it worked. How?
In your master page, define your image and add runat="server"
<img src="put your default image.jpg" runat="server" id="changingImage" />
In your content pages, do this
protected void Page_Load(object sender, EventArgs e)
{
HtmlImage img = Master.FindControl("changingImage") as HtmlImage;
img.Src = "~/images/imageForContentPage1.jpg"; //replace this image based on your criteria
}
Possible exception is Null Reference when the name of the image control specified in .FindControl could not be found. Make sure it's exactly as you named it in the Master Page. And to prevent a Null Reference Exception, wrap a check around
if(img != null)
{
img.Src = "~/images/imageForContentPage1.jpg";
}