Hi, Spencer. Thanks for giving us the opportunity to answer your questions about the upgrade.
1. The functionality that’s built-in is for the featured image to display in the event tooltip on hover. We do have a tutorial that will display images in the List Widget if that’s helpful: https://theeventscalendar.com/adding-post-thumbnails-to-the-events-list-widget/.
2. The events are custom post types and not in a database of their own. As such, it would probably be challenging to set up syncing between two sites.
Hope this helps you making your decision!