My personal game plan is to always buy properties that have some sort of value creation opportunity outside of waiting for appreciation.  

Our first property was a family home, we paid 90%MV, it desperately needed up dating, after a $20K  - plus my sweat - reno on the inside it looks brand new, outside is still the same, but there's no work needed. 

Real estate is already a very tax-efficient investment, making it suitable to hold outside a Roth.  

I'd waive a carrot of 10 $20s outside the window.

It is going to depend on your goals, you mentioned you are looking for cash flow, not all markets outside of CA cash flow.  

Do I have to look at each property individually to know the value of the property, outside the assessed value given it by the county.

Once had a discrepancy where they measured the outside walls versus the inside walls.

The other areas outside of NCA will not have as much upward equity growth as CA.

The branding in particular would be done in the content that I produced to advertise the open rooms along with physical branding on the outside of each house (ie distinctive color accents and perhaps even an led sign).

I am from the NW suburbs outside Chicago, and am on the very beginning of my real estate journey.