Thank you for sharing your experience.
I want to assure you that the desire to avoid breaking changes has a solid basis in the way business operates. People want to never have to change a single line of code when upgrading, and we must respect that.
The problem with adding properties is that they make things difficult to control and configure, and the more properties you have, the more scenarios and combinations you have (exponentially more), and this makes the chance of having bugs or errors much higher, because a controls becomes impossible to test as one can't foresee all possibilities.
That said, we have shown a way to edit checkboxes with a single click in the following article, so you may find it useful: https://docs.telerik.com/devtools/aspnet-ajax/controls/grid/data-editing/edit-mode/batch-editing/how-to/editing-checkboxes.
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