Since there is one rendering for many items you can almost follow Amit's answer but you will need to use an edit frame. Glass has a method that helps start an edit frame in mvc. For more info about incorporating that see the following link: https://visionsincode.wordpress.com/2015/01/08/how-to-use-editframe-in-sitecore-mvc/
You will have to pass the edit frame helper the current item that will have the checkbox to change and the id or path to your custom experience button. My example item: https://www.screencast.com/t/y3WnJod3
@foreach(var bannerItem in myBannerList)
{
using (Html.BeginEditFrame(bannerItem, "{FDE5A219-C691-4978-B9D2-939E98582626}")
{
...banner html here...
}
}
Your id will be different and should be maintained in a constants file instead of as a raw unnamed string but this should demonstrate the idea.
There is another more elegant option too but it takes a little more work and I have not actually tried it myself. You can create an Edit Frame Small Button and give it a command. You would then assign this button to the edit frame instead of the one shown earlier. This type of button takes a command which you will want to insert into the command section of Sitecore's configuration through a patch config. It would be worth while to make the code the command points to somewhat generic in that it should read in a parameter for the name/id of the field that it will try to toggle. This method allows a user to simply click the button that appears on the edit frame and toggle the checkbox. The other way opens a modal which displays the checkbox field.