In the 2024 insurance market, CA is hard to place, so even though you could force them onto a single policy, it may be more economical to keep them separate.I'll send you a note with the carriers who can do this for you.

*I know the markets really well even better than some local agents.

Is there anyone in your local market you could take out to lunch who does flips?

SF is a very unique market, and actually may be a great time to buy right now, especially if they can successfully turn the city around. 

As for your ques if to wait, well, it depends on the market, in some parts of the country prices are still going up, slower, but still going up, other parts the prices are coming down, you know that area, what is happening there? 

I was involved in a bunch of industries—from wellness and gyms to digital marketing and consumer products.

A sellers market in general.

Hi Nate, I'm new to "Bigger Pockets" and new to the  real estate market.

@Denise Lang - would NOT recommend my local market right now unless you can source it off-market. 

While I do maintain a relatively modest percentage of my assets in money market instruments, corporate debt funds, and high dividend stocks, I remain most comfortable with the investments I specialize in and know best.