I dig deeper into the regs on the city’s website and it seems like both long and short term rentals are allowed so not sure why I was told otherwise over the phone.  

My biggest concern is the flood certificate says the main floor of the property is 3.7 feet above Base Flood Elevation.

It's a plus if they offer any good bundling options for an umbrella policy for 2-3 homes, as we're looking to get one for the first time.I know some insurers have been leaving the CA market recently so looking for updated recommendations based on your personal experiences.Thanks!

Qualify the seller quickly on the phone and schedule an appointment to see the property. 

Will you want or need to rezone based on what you wish to build?

Hi Matan-Great question.I work with many physicians in California.The thing to do is find an investor friendly Realtor in the area you wish to invest.I am based in Ann Arbor, Michigan.

I say you should weigh those options for yourself based on research.

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

Set a goal, work backwards, and create a realistic strategy based on your personal abilities.An aggressive investment strategy can get you free from your 9-5 in about 3-5 years.

That being said never base your offer on the other guy.