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There are two schools of thought about training and racing. The old school was train hard so racing feels easy. The modern school is train easy. A benefit of the old school was that you put in ehough time at high effort and when tired that form was maintained in high efforts and when tired...

I don't carry much. My tool kit is not much larger than 3 tire levers. I seldom use them. I carry 2 tubes in a plastic bag. It all fits into 1 pocket. But in the distant past, when I was doing long solo rides, I carried more gear and had a seat post bag. One good reason for putting tools in...

I knew people who could do it at speed. I always found it easier to avoid situations where I had to rely on the limits of my abilities of braking or steering. If you are riding "fast" a foot behind someone where somehting bad happens to him, you are going to be part of that badness. I don't...

As I said I will let you deal with your personal problems on your own.

Pain goes away with experience. I don't think you have enough miles in to feel comfortable with a long climb. I think the typical climbs in your area ar 6% for 6 miles (2000'). Since you were in your lowest gear, I would suggest buying lower gears. I will be in Menlo Park in about a week...