As a Peninsula guy, my suggestion would be to meet at lower Skyline and 92.
Assuming you are on 92 headed west, you will be in the left lane as you approach 280. You will proceed through the stop light under 280 (this the light for Canada Road) go up a brief rise and then head down toward the reservoir. There is a stop light at this intersection (no more than ½ mile past 280), with lower Skyline going north. This is a popular place for folks to park although I do not believe it is formal Park-n-ride location. The stop light affords the opportunity to have the waiting cars fire up and/or the group to pull over.
I don't know if Randy is referencing this area or the parking area at Canada Road as it is truly at the intersection of 280 and 92.
I would not recommend the top of 92 at Skyline, although there is a turnout at Skylawn Cemetary that could handle a lot of cars, as you are dealing with merging a bunch of cars into the flow of traffic.
I wish that we did not have a prior commitment so that we could join you. Sounds like a great time. Thanks again to Larry for coordinating things.
Just my 2¢
Tom
P.S. Scenic ride home - what about heading south on Highway 1 to Pescadero (Highway 84) up to Skylonda (lots of motorcycles and cops) down 84 into Woodside and follow 84 to 101 and then down to the Dumbarton Bridge and east from there? Just another option on the Peninsula side.
Please be aware that we are looking at a west Bay trip, probably in early September, that would start with breakfast at 35 & 84 (Alice's restaurant), head to the coast with lunch in the general Santa Cruz area. Still working on those details - more to follow.