I can tell you that I have a Surface Pro 8 with a Logitech wireless keyboard attached, and I still have checkboxes all over.
I can expect that with the onscreen-keyboard, but with external keyboard it should NOT happen.
Personally speaking, I would remove the checkboxes in any case, as even in tablet mode I like to double-click my icons as I use to do with my mouse.
...but this is not an option for us users....