Nice clouds that day. How would you rate the difficulty of the trail? I was apprehensive in June (mainly because I was by myself) and did Ophir Pass and Red Mountain instead. They were easy.
Easy/Moderate but that is subjective. I would recommend going up Yankee Boy on the way to Imogene. If that seems easy to you then on the way back you can start up Imogene. If Yankee Boy seems difficult dont go up Imogene. Also don't be afraid of heights/drop offs or having to backup on ledges if need be.