Wow, thanks for all that. I had just come up a short 3.5% hill and was most likely 3 gears up from the lowest. The hill meets another road at the top where I turn left and head back down a short drop before heading back up another rise. I ride this loop daily now and I always do the same thing coming up this hill. I hit the top, turn left, and as I head down the short drop, I shift from the inner ring to the outer ring to build speed for the ensuing rise. I may have mistimed the shift and was putting too much pressure on the chain at the time. Or maybe I just didn't push the shift lever far enough before pedaling hard again.
I'll be riding the same loop again today, so I'll pay closer attention to ensuring the shift is complete before adding pressure again.
On another note, the Brooks C-17 saddle seems to be helping. Much less pain. I also raised the seat height another half inch, so I'm at the height the LBS wanted me at when I first got the bike. I had them drop it down a bit until I got used to the new geometry. So between the new saddle and the higher seating position, I seem to be doing better. Still fighting hand/wrist numbness after an hour, but that goes away if I stop for a bit and shake out my hands while grabbing a drink.
And I'm down 20lbs since I started riding. That's the biggest reward in all this.
