I currently live in SF Bay Area as a renter. I'm feeling uncertain about my next real estate purchase to house hack. I can do either of 2 actions:
1. Buy a 3bed/2bath in a waterfront property in Benicia, CA & get 2 new roommates to pay off mortgage. No matter the property this definitely will negatively cash flow because this is SF Bay Area.
2. Buy a duplex to fourplex in Portland, OR or Vancouver, WA, save more by not paying any state taxes, & find a tenant for the other units. This has a greater chance of positively cash flowing.

If you can take your job to be fully remote full-time as a single person without kids, what would you do? I wouldn't buy a duplex anywhere in SF Bay Area because they start at $800k+, which is ridiculously high price point. If you've moved out of CA in order to buy more affordable real estate in Pacific NW or TX or literally anywhere that's NOT a HCOL coastal city, do you have any regrets on that decision?

I think the stumbling block you may run into is that this job allows you to be fully remote, but what about the next one, there aren't many places that pay Bay area salaries that aren't HCOL.  Can you do it yes, but you might be just as well off staying put and investing OOS to get the cheaper property exposure and still stay near a high paying job center like the Bay Area.

Have you run the numbers on both scenarios? That's usually the easiest place to start to start taking out some of the guesswork. For househacking in general, here are things to think about:

https://www.biggerpockets.com/...

In this case, I don't think either scenario you're posing will cash flow, so I'm not sure moving based on these would be worth it. If you were talking a fourplex in Indiana or somewhere, that'd be a different story. But mostly, I'd say run the numbers on these. The option in CA--I doubt the roommates will pay enough to make much a dent in the mortgage (that's going to have to be a heck of a mortgage for the kind of property you're describing), and you're also stuck with roommates for quite some time. Just things to think about. The alternative is to not force yourself into househacking and just buy straight investment properties.