I'm not going to guess about the why, but you can simulate a mouseclick on the inputs (checkboxes) in the listview to get it to work.
When you check checkbox through javascript, checkbox will be checked only visually, the underlying entity attribute will not be changed.
The best solution could be to change attribute value itself in microflow or nanoflowin (if no commit required), which will replicate changes in Window as well.
You may also want to use new checkbox functionality for mendix version 9.24
Check out following link
https://www.mendix.com/blog/mendix-release-9-24-what-a-ride-it-has-been/?utm_medium=social_owned&utm_campaign=Mendix-release-9-24&utm_source=linkedin.com