Just a suggestion but what I have found to be the most efficient `cupboard' is actually a very deep sliding draw. With cupboards you can never get to the back to easily retrieve that pot. With a large draw it is all acesible. They make good quality slides nowadays that can take the weight.
The cooler could also be on a sliding platform to enable easy access and to relieve you of having to clear the top counter every time you needed to access it. Coolers should be the biggest you can get away with. The more ice you can put into it the longer they keep the food cool. I would not recommend draining the melt water until absolutely necessary. The water contains great cooling potential as it should be close to zero degrees celcius and you would be throwing away a lot of cooling time.
If you plan on more than a couple of days away you will probably have to resort to purchasing block ice then you will have the hassle of water in the cooler. Having a raised compartment to keep the food out of the water would be a good feature. Big problem with ice coolers is when you have some meat that leaches blood and gook into the water. You are faced with a major cleanup and sterilistion (bleach) job ahead of you so you must figure on how to safely dispose of the drain water so it doesn't get into the bilge.