Cleaned out my home office and been doing some retirement tub organizing.
Free Tip: if you ever decide to amass a large collection of cigars do not buy anything but boxes.
I hear ya there, contemplating building some trays for my tub to be able to access everything in there. Too difficult to get to it all
Purchase some cedar cigar trays. $14 ea, or a handy guy like you might build some out of an old barn door.
Purchase some vinyl coated wire shelves and cut them up into small stands to put between the trays as you stack them in the coolerador.
Add gel, beads, or whatever for humidification and a digital temp/RH hygrometer, good to go.
Depending on your cooler you'll still have room to fit a box or two at one end.
I have two set up this way, holds the RH rock solid, easy access to all the singles.