Oh man...I love your current box! I kinda sorta collect vintage wooden crates/boxes, especially military ones.
I know what you mean though about diggin' for stuff. It really gets old when you need something in the box quickly. I have a similar box in the back of my Rover, it's about twice the size though width wise. I keep tools, jumper cables, recovery gear and such in it. It can take awhile for me to find anything in it.
I feel your pain in re "can't even start a project without something going wrong"; that's the story of my life.
As to your build.... if you are interested in some additional design and build ideas you might want to check out the "Expedition Portal" forum. There is an entire section devoted to ideas, tips-n-tricks and such for kitchen chuck boxes.
I look forward to seeing what you come up with.