Deep down, he worries he’s not successful, confident, or attractive enough to "deserve" a beautiful partner.

The first step I'm doing is checking with the city zoning to see what they would allow before I get too deep with looking at plans, financing and construction. 

Given it's location not far from the ports of Richmond and Oakland, and that the Chevron oil refinery is nearby as well, some of that is likely be driving the highest and best use assessment. chris in the deep south they turn the anchor store into a big church..  

FD came and red tagged the outlet.

Once you are familiar with what a good investment looks like, then you can create a rule of thumb to help you analyze property faster and only dig deep on the ones that look promising.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

I compare that to the trulia crime map and stay away from the red areas.  

Red flags yet?

Great question Todd, first red flag is asking for full payment upfront.

As a matter of fact, the red 4 unit next door is always on Zillow trying to be sold.

I did all my other due diligence like asking for paystubs, W2s, Tax returns, Employment verification, bank statements etc etc and did not see any red flags overall.