Do you think there’s hope?

Out there, I would say you have one main target demo: vineyard owners. Having met a few of them, this is what I learned: some live out there, some split their time 50/50 between SF and wine country. Some only pop in once in great while (never met these ofc) and leave it all to a manager. A lot of them know each other and work together to further collective interests. So you'll need discretion.

All of them are treated like little mini-celebrities once people know they own a vineyard in California wine country. (only happens when you're physically in wine country)

how can I be more appealing out there?

There's a thin but steady stream of pretty girls who decided they want to live/work/intern on a vineyard you would be competing with. You could simply enter that stream, i.e. work on a vineyard. Avoid the extra-touristy ones like Castillo di Amorosa as you'll never see an owner at one of those.

you could also find their names, look for events they'll attend, and try to freestyle . That'd take some massive courage.

That said, there's probably a few other POTs from the hotel, restaurants, or some other random industries out there. Seeking is still the best place place to find them.
Wine country tourists are almost never looking to sugar.

Travelling to SF is an option, you'll have many many more choices but its gonna be a hike. Russian river valley is close by but meh, not much wealth concentration.

Best a luck!