When you get into larger (5+ units), mixed use, renovation, vacant buildings, etc. they will need to access commercial policies.  

They likely have a policy that only one vendor is approved, because they know the quality of work and it guarantees consistency.

My question is this:  If I buy a property from an owner who has had the property for 30 years, he / she has already depreciated it to zero. 

Just get an umbrella insurance policy until you grow your portfolio large enough.

Has anyone run across this new policy and it sounds like I should stop paying my local and state as VRBO is doing it on my behalf?

Once investment company obtains title plan is to sell property to my sonMy goal is for my son to buy the property for zero out of pocket and for my investment company to get a fair return and pay as little or no taxes on the gain.

Retroactive tax policy is terrible and shakes confidence in the system.

I'd be careful with that advice.4-Lastly, there is NO LIMIT on the number of homes you have financed if the home you are financing is your primary residence, conventional guidelines only limit  Second home or Investment properties to 10 financed properties.In short, you should be good with either FHA or Conventional loans in your case.Here's the guideline straight from Fannie Mae https://selling-guide.fanniema...Limits on the Number of Financed PropertiesThe following table describes the limits that apply to the number of financed properties a borrower may have.Subject Property OccupancyTransactionMaximum Number of Financed PropertiesPrincipal residenceTransactions other than HomeReady loansNo limitPrincipal residenceHomeReady loansDU and manually underwritten - 2Second home or Investment propertyAllDU - 10Exception: High LTV refinance loans are exempt from the multiple financed property policies.

The policy is also referred to as a "Dwelling Fire Policy" but has the necessary endorsements and limits required by my lender.

Absolutely look for a private landlord as they are not bound to corporate policy and can use judgement.