After some research, I am opening this issue up again. I think this proves beyond a doubt it is not a plugin issue. It is in the war file itself.

I went to https://get.jenkins.io/war/ and began downloading old war files.  I checked images/24x24, looking for terminal.gif.

In version 2.332 the file is there. In version 2.333, it is not. I found the cutoff point!

I checked the changelog for 333, and I believe this is the change that broke it. https://github.com/jenkinsci/jenkins/pull/5778

On the dashboard default view screenshot in attachments, you will see how it looks without terminal.gif. Looking at the HTML, it is looking for 

<img border="0" src="/static/66c2a804/images/24x24/terminal.gif" alt="Console output" title="Console output">

My workaround has been to copy the missing files into war/images/24x24 on my server and restart the service. The images then appear correctly.

 Many other icons are missing from the personal view plugin when installed on Jenkins 2.333 or newer.