Never understood why wake boat mfg did not put more, larger and better placed cleats on boats.
If you want to make anchoring and rafting easier, I would install a single 8" pull up cleat horizontal between the backrest and nav light.
A 6" slim line on each side should also work. They do that with some current boats.
Find someone with almost any fiberglass skills to reinforce underneath and "peanut butter" in an aluminum plate like people do when adding a tower.
Cooler style and size are dependent on how much you need.
I have found the Igloo Cube to be space efficient and more comfortable to sit on with the higher sides than a standard cooler. I don't like the wheel models because it is too much of a space waste on the boat but I don't have to haul it very far and I am not a puss.
1991 MariStar 240sc, 454, tower, WetSounds, Krypt and Rockford Fosgate