As a newbie (owner since 9/2018) and some SLO county residency under my belt, maybe next year I can be of more help in planning, like reserving a private setup at a local winery, with of course a great road to get there (See Old Creek Rd. between Morro Bay and Rt 46) as just one example.
A place like the Estrella Warbirds museum in Paso Robles has car clubs arriving all the time for visits and photo shoots. I'm a volunteer over there.
I'm organizing this year's rally and unless I completely blow it and get flogged to death I will probably end up doing next year's rally as well. I'll send you a PM with my number if you could reciprocate in kind we can talk and come up with a nice midday stop. If there is a hanger we could use at the airport for a lunch that might be real cool. I believe I have now driven almost all of the roads out there between 101 and the 1, 41 to 46, and all the others in between and beyond.