Rob,
I noticed some staining on the bottom of your wood, next to the roll up doors. I have something similar on my walls. I was making all sorts of plans to grind down my concrete, add weather stripping and even build a roof over the door to keep the water out.
A client had the same problem and asked me to fix it. I don't know why, but I got to searching online for ways to stop water from getting through garage doors. I found this
Amazon.com: Sensible Solutions 3016 Storm Shield 16-Foot Garage Door Threshold: Home Improvement and really liked the reviews.
It came with a full tube of liquid nails to glue it down, but it's not called liquid nails on the tube. I cut it to fit, glued it down and then shut the door to hold it in place. The next day I bought a tube of brown silicone and built up the ends to form a dam of sorts, so water could only go back outside. I went pretty heavy with it, and still only used less then half the tube.
Shortly after doing that, we had a very strong storm come through that dumped several inches of rain. I went over there the next day to see how it worked, and was VERY IMPRESSED that thre was no sign of water in the garage.
I bought one for my shop and put it in the day it arrived. I did it the same way, and I've had the same results. It made a HUGE difference in water getting in under my roll up door.
Eddie