They are worth it if you need to do what they can do, which is keep food cool for a long time without having to add ice.
If you are just chilling beverages, and are where you can add ice as often as needed for that job, then a cooler sturdy enough to handle the load should be adequate. $200 to $1400 will buy a lot of ice, and the ice will go almost as fast in the expensive cooler as the cheaper one if what you are doing is throwing in warm drinks every day (or more often) to cool them down.
I find that my 30 year old Gott Tote 12 (drinks for one person, one day) and my 45 year old steel Coleman are much better made than some of what is sold today under those brands (Coleman no longer manufactures most products, it is now just a brand for retailing). I would probably have to spend at least $300 today to buy something to match the old Coleman.