What: Hill Climbing
Why: It's a quintessential scene of one bay side town of which I love seeing photos. Though I've tried on several occasions to pick up shots of this city, the demand and prices have tended to put me out of the running. I saw this and wanted it, but was actually surprised to win it!
When: August 21, 1954 based on the writing on the mount.
Where: San Francisco, CA. Pretty much a no brainer. The cable cars are on the California line, and some research reveals this to be in the 700 block of California Street, which provides an impressive view towards the Ferry Building at the foot of Market Street.
Who: A few folks here and there.
How (much): Interestingly, I got this for under $7. In looking back, it was labeled "SF" instead of "San Francisco" which likely helped limit its exposure to others who would outbid me.