Image issues with widgetized template

I am having a really weird image issue. I wanted to make sure I compressed my images so I tried to replace one of the images I have on the homepage using the widgetized template.
I can see my image in the media library as well as FTP and in the browser using the url of the image but not on the page itself. When I change the template to default for the homepage, I can see the image but I want to use the widgetized layout. Any suggestions for why this is happening? Also I noticed when I upload images now sometimes they are not in the correct month folder, hence, the url should be incorrect yet those images still show. (Also I am not using the featured image for these pics)
I’m so confused. Any help is greatly appreciated.

https://www.sacrealtor.org/events_center/

thanks