I have a couple short cord tools. Hand-held belt sander ate its own tail, gave me the idea. Tools that have that kind of appetite probably make the most sense. Circular saws and jig saws, sometimes the plug gets snagged in the cut or on the edge of sheet goods. Easier to keep clear if it's where you can see it. For drills and screw shooter, especially overhead, you need some reach without the bulk of the plug, so I like them long. I drape a loop over my shoulder including the plug when possible. When you store a hand held tool, the main issue is how to loop that cord, isn't it?
I really like Duker's solution. You could have a few extensions of different length. Besides job site safety, all circuits lose power the longer they are. You can make up for it a little with a heavier gage wire, but for max power, you should use the shortest that's practible.
For stationary tools, it's cord management. If your equipment is mostly up against walls, looped cords aren't really a tripping problem. But if your equipment is more central, and you mostly run one machine at a time because you work alone or have a limited number of circuits, the overhead reel seems like a good setup.
I think the idea may have come from air tools. How many of those have you seen with 6 feet of air hose permanently attached? One of my favorite features of my Milwaukee Sawzall is the twist lock cord. Sort of wish every tool I owned was like that, then three or four cords of different lenth - presto - no extension cord needed!