If you want to add a checkbox for each product on your listings, first you can change the option "Display the quantity field on the product page" of the configuration to "global on listing".
That will display a quantity field for each product with a global add to cart button at the bottom.
Then, you can edit the file add_to_cart_listing via the menu Display->Views and hide the quantity field (with a display:none for example):
<input id="hikashop_listing_quantity_<?php echo $this->row->product_id;?>" type="text" style="width:40px;" name="data[<?php echo $this->row->product_id;?>]" class="hikashop_listing_quantity_field" value="0" />
and add next to it a checkbox with some javascript which will change the value of the input field when the checkbox is ticked or unticked.
I think that it will be the easiest.