I"ll try to answer some of your questions. Jackie has some records from about 1990 on that might answer more of them.
I first started racing with the SSS in 1985. At that time the membership was small and sailed an eclectic fleet of mono-hull boats ranging from a ferro cement ketch to small 20' wood and fiberglass sloops. I placed in races in my Coronado 25 and not with the best racing sails. There were several multi-hulls ranging from Peter's Antrim cat to a wooden tri. The faster boats got to Finish Lines long before a struggling Coronado 25 and often early Finishers went up to the race deck to help out.
In many ways, things were different, including the clubs. The VYC, OYC, and GGYC were still in their old buildings. Both the OYC and GGYC were much more casual about protocol. When the Corinthian Race started, so was the CYC. The Corinthian Race Awards were handed out on the CYC deck following the race. Informal post-race gatherings were the norm, as were the SSS meetings. The HMB race ended in a bbq and the awards were left over awards, which were often "utilitarian" things like seat cushions, fenders, flashlights, that remained unclaimed from the other races that year. Winners got to pick from the litter. The SSS was much smaller, everyone know most everyone, and the competition was less cut throat than I sense it is today.
The courses have always been long, with long legs between marks. The original Vallejo 1-2 Started and Finished at the Golden Gate YC, with Blossom Rock as a turning mark. Some early ocean races Started and Finished, or at least Finished at the Oakland YC. The original Corinthian Race used the now departed Knox Buoy as the turning mark for Blossom Rock; there was no finish leg out to Little Harding and back. The East Bay-Estuary Race Finished up the ditch at the OYC.
No, doublehanding came later. As I remember it, all the SSS boats were singlehanded early on. When the 3-Bridge Fiasco caught on as a popular race marked a turning point in double vs singlehanding. There was considerable angst over whether to allow doublehanding in all SSS races. There was even some discussion of a doublehanded division in the "Singlehanded" Farallones Race.
About finishing. Again, as I remember it, most boats finished. Sailing singlehanded out and back to the Farallones and Finishing was thought to be an accomplishment. Just finding the damned island in the fog prior to GPS was an achievement. The time limit for the Farallones Race was Sunday, and on several occasions racers anchored off China Beach, slept for awhile, and Finished on the next Flood. There were parties at Vallejo, the GGYC, and the OYC following races, so if you got there late, there was usually something going on. There was no "overall" season champion; each race was an individual effort. --Pat B.