Hi Jason,
Thank you for sharing these details.
Based on some testing and research, here are my findings.
Currently on your website, the template for the single 'Businesses' posts is being controlled by the Elementor.
A Toolset content template named 'Loop item in Map' is also assigned to the single 'Businesses' posts, but it is empty and is being overridden by the Elementor's template, anyways.
( screenshot: hidden link )
Elementor Pro, out-of-the-box doesn't support conditional assignment of templates, based on the custom field values. But there is a paid extension 'The Plus Addons for Elementor' which does support this:
hidden link
Another alternate which doesn't involve another extension, is to not assign any Elementor template directly through the Elementor's theme builder so that the Toolset's assigned content template is used to display the single 'Businesses' posts.
Inside this Toolset template, you can conditionally load the required Elementor template through their shortcodes and Toolset's conditional display feature:
( ref: https://toolset.com/documentation/legacy-features/views-plugin/conditional-html-output-in-views/ )
[wpv-conditional if="( $(wpcf-premiere-listing) gte '1' )"]
[elementor-template id="2396"]
[/wpv-conditional]
[wpv-conditional if="( $(wpcf-premiere-listing) lt '1' )"]
[elementor-template id="82"]
[/wpv-conditional]
In the above example usage, when the value of the 'premiere-listing' field is greater than or equal to 1, it will mean that the checkbox is checked and the Elementor template 'Premiere Businesses' will be loaded.
Likewise, if the value is lower than 1, it will mean that the checkbox is not checked and the Elementor template 'Single Business' will be loaded.
I hope this helps and please let me know if you need further assistance.
regards,
Waqar