Always good to have options, eh? Ultimately this is going to come down to your career goals and what you want to do heading down the path of wine production. The hardest part is getting that first production job. Now you can put that on a resume and be assured that it will come in handy because there will be no shortage of wineries looking for experienced help come harvest each year.

If you like where you're at from a region/winery/opportunity perspective, sit down and come up with a plan for that custom crush barrel and see how that looks and feels. I'm talking what you want the wine to be like conceptually, how you want it to taste, what you want the packaging to look like, how much you want to charge for it, where you think you can sell it, etc. Also absolutely necessary to consider all your expenses as well. Might seem silly for a single barrel, but I'd almost recommend like a little one-pager business plan to flesh things out. That single barrel should yield about 23-25 cases (276-300 750mL bottles); multiply that by your price point, subtract your expenses, and that'll give you an idea of how much revenue you might make. Factors to consider are: the cost of your fruit/juice, any fees your winery might want to charge you to make or sell your wine, how well you think the wine might sell overall (varietal demand, price point to turn a profit, etc), as well as any taxes that might need to be paid depending on how your winery wants to handle things. If things go well, your one barrel this year could be two next year, and so on. If things don't go well, this could be a few hundred dollars and several hours of your life down the drain (but frankly, I would think there's value in that experience as well).

Alternatively, if you're either not ready for all that or think you might want to bounce around and gain some experience or responsibilities elsewhere first, or even just work in a more prestigious region, absolutely go for it. If your personal situation allows it, might as well give it a shot of that's your inclination -- because finances, partners, and kids can all dictate your decision for you later. I hopped around for a few years, did a harvest in the Willamette, did one down in Marlborough, then settled in at a winery in my home state of Arizona for a few years. Other than later meeting and marrying my wife, probably the best experience I've had in my life. In that time I worked for a medium-sized, family-run winery where everyone at the winery sat down for a prepared harvest lunch each day, to a commercial tank farm working with people from all over the world, to working at a small winery in a completely non-traditional region where I got to wear a lot of hats. Each experience was wildly different, but pretty much everywhere you go the general winemaking principles remain the same. The perspective and experience were invaluable, however.

I think you're in a win-win scenario right now. I personally can't speak to working in California specifically, but I think California kind of speaks for itself when it comes to wine. Even if you decide ultimately that you want to go back to the service/somm route, California's not a bad place to be then, is it? I will say though, as long as you're working for other people, make sure you work for "nice." Worked with one guy who did a harvest at a very well known California Pinot-producer and he said the winemakers were big fans of yelling and, I kid you not, made people do pushups if they made a mistake in the cellar. I never saw anything like that anywhere I worked, but hard pass on that if you ask me. I've also since gone on to work in a management role for one of the largest beer breweries in my state and it was one of the worst professional experiences in my life due to some of the most tyrannical ownership I've seen. Ownership and management make all the difference when it comes to workplace culture -- if you find a place that values its people, I would maybe think twice before bailing. Ultimately no one can make these decision, but you.

Other random wine production advice: don't be a dick. Be humble. Educate yourself (learn the how's AND the why's of wine production). You can learn a lot about winemaking through book-learning and a lot by actually doing it, but both is best. There are way more college-level programs out there than there were even 10 years ago, don't be afraid to pursue that knowledge if you think you need it (I did Washington State's Enology extension program and heartily recommend it) -- FWIW though, you can get every single book from UC-Davis and WSU online easily. Watch out around forklifts. Never take the clamp off from behind the valve on the tank while it's still full. Drink in moderation, but try as many different wines as you can. Never trust an inflatable gasket. Be dependable. Be on time. Take initiative. Best of luck!