Actually, you get end of listing notifications via email - that is my trigger to act.
If you look at your "selling" page, each listing should have "Assign automation rule" in the pull-down menu on the right. I subscribe to basic "selling manager" and perhaps that gives one this feature. Also, you might be able to bulk assign a rule.
The reason I don't automate this is inventory control. Every time something relists, I need to adjust my inventory.
Also, if we have 10 of an item, 5 sell in 30 days, the listing automatically renews (10 items again) and and more than 5 sell before I catch it, I have some explaining to do.
The way I do it, I have control. Given, sometimes items are "out of stock" overnight before I get to relist but, for me, that is lesser of evils.
Bernie