If not, you can always increase the rent to market value, but my guess is it being California, there are limits to rent increases.There are rent caps but they do not apply to single family homes owned by individuals (not LLCs or Corps) 

Here's what I'm accounting for currently:Mortgage (P&I)InsuranceTaxesElectricWaterTrashInternetVRBO/Airbnb feesGeneral/RepairsCleaning (though these will be passed through)If i'm super conservative on my monthly rate, I will need to rent the unit 10 nights/month to break even, if I am more realistic with the rate (according to my realtor who runs two STRs), i'll need to rent it 7-8 nights/month to do so.

What do you feel your greatest need is as you transition from single-family to multifamily?

Grade B-C single family home. 

Also, multi-unit sales involve more legal and financial nuances than single family homes so it will be in your best interests to work with an agent.

Its super simple.

It is improving, meaning sellers and builders are facing a little more competition, but there is still a shortage of housing units in the region. 3) Rental prices are strong and single family homes and townhouses rent very quickly.

Access to Larger Loan Amounts: Cross collateralization allows borrowers to leverage multiple properties, which can lead to a higher overall loan amount than what might be possible with a single property.2.

MLS is pretty good for single family comps because most people list their home with a Realtor.

Depending on where you are looking, inventory for 1-4 units can be a challenge as a lot of the NW suburbs are all single family homes unless you are further NW like Rockford or Elgin or something like that.