I don't own nearly as many lenses (only about twenty primes and ten zooms) but I know the angst of picking just one. To liven up my daily commute, I take a camera and lens with me and do some street photography. Not while driving, I hasten to add. I use public transport.
Picking a camera is easy, my Samsung NX1 just rocks for this application. Now I do have three NX mount autococus zooms, but that gets boring. So I use a K mount adapter for it. I have
a lot of several prime lenses that can be used for street photography: 8mm fish, 20mm, 28mm, 35mm, 50mm, 85mm, 100mm, 135mm. After some experimenting I tend to take the easy way. That is my SMC Pentax M 28mm f/2.8 - great colors, sharp, easy to pre-focus, just wide enough on a crop body. What's not to like? The problem is that I tend to get the same shots as before.
Picking a lens at random every morning would certainly liven things up a bit. Great idea.