For what it is worth, here is another opinion. if you can handle the higher cost, Yeti in my opinion is the best cooler for most of us boaters. If you want a beverage or steak still pretty cool on that last evening of a long multi day float, Yeti can give you that but as mentioned it is gonna cost you. Cannot remember the name but I read about an Australian cooler that beats the Yeti brand on keeping things cool but cost makes the yeti's look reasonable in cost.
For less money you cannot go wrong with other brands like Canyon, Engel, Grizzly, ORCA and others listed here on the Buzz. Take your pick. All will work pretty good. Just find the best deal or on sale units. Watch the descriptions and get the thicker top and side insulation.
I have added extra insulation to the cheaper Igloo / Lifetime coolers (both glue on and injection) and with good cooler management they will work pretty good at a lot less dollars invested. For short length trips - no problem. For the longer multi day floats you need coolers with thick top and side insulation.
Regardless of brand, I always glue on thick (usually one inch) closed cell foam on top of my coolers plus a closed cell pad sized for a snug fit on the inside of the cooler on top of the goods. If the sun is out, if we get to camp early I will also toss something on top / sides of my cooler just to keep the direct sun off the cooler.
I have used drag bags quite a bit. On some rivers drag bags work pretty good. For me, it is worth the extra cost and attention to reach into my cooler at take out for the day and get a clean, no dents and cool drink.