Keeping a neat Shop...

My review at my first ever "real" engineering job said something like:

"Paul Moves his assigned projects directly to the desired result with exceptional speed and skill leaving a trail of destruction in his wake."

This was a job where we built real prototype hardware controlled by electronics and
some of the earliest embedded computers. (6502 anyone?). I got the Job done but I left a wake of debris behind. Not much has changed. My rocket shop occupies a two car garage and a 8x10' office at my home. I find the continuous mess and inability to find things is probably the biggest frustration in my life.

I intellectually realize that I'm whining about my own personal shortcomings and should just gut it out and clean up my space. In my life I've never achieved that for any period of time measured in units longer than an hour. So I'm asking my readers if anyone has successfully overcome the this particular demon? I'm open to suggestions?

Its really a two part problem

Part One I have way to much stuff crammed in too small a space. So it needs a Major organizational redo. ( I can actually envision someday solving this part of the problem.)

Part Two once everything is organized how does one maintain cleaned up?
The Failure Scenario goes something like: Come home from work, family is going to have dinner in an hour so I go out to garage and start machining a pressure test plug, then dinner is called and I go in and eat... not to return to that project for a few days. This is complicated by the fact that I often have half a dozen partially finished projects in work at one time and I work on the different projects as I'm inspired to do so. This is not a complete failure as I actually do finish a significant percentage of what I start. (It may take 12 calendar months on a project that is only one real week of work)

Some specific questions for comment:

How do you handle partially finished projects in a way that you can efficiently task switch without leaving piles of half done all over the shop?

How do you decide when to throw something out?
Our current rule is if it is not a tool and has not been touched in (Replacement Cost /25) months it goes in the trash. If the value is over $250 it goes in the ebay pile... (The Ebay pile may someday actually make its way onto ebay)

How often do you redo your storage systems.....
How much dynamic range to you leave for expansion?
IE I have a drawer for AN male elbows. When I create the drawer its 25% full, a year later its over full and won't close so it sits on top the pile....


Has anyone ever tried to hire someone to clean up/ maintain their shop?
How did that work? How did you find such a person?
In So Cal one can find lots of low skill labor that will follow directions, but I think I really need someone that knows the difference between a drill bit and a mill bit, a servo and a valve etc...

Do you think it would be possible to hire a Science/Tech interested high school student to work on this without leaving them emotionally scared for life?