Its annual STR rent is likely more than it would cost to rebuild the duplex (Peak rent is ~$350/unit per day = $700/day for the duplex, Minimum rent is $80/day per unit - it is rented virtually every day).The fear is San Diego STR regulations. 

I also really wanted to take the leap, and get into something, out of fear of not getting the guts to start!

I think it is mostly fear but....Anyway I can go on and on. 

Think it believe it know it act like it act based on this and before no time they are trying to stalk you spying on you wondering how that damn monkey did it.Yeah  I see you  !

I fear that if I go to apply, and do things the right way, then the city will deny me and I will be under their radar.

Sounds like you are thinking about things correctly and don’t fear good debt that produces cash flow.

Fear might hold you back. 

@Dan Heuschele Your right, landlords are not required to accept emotional support animals, however most landlords seem to be in so much fear of the Fair Housing Act that they throw logic out the window.

If you show your wife the increase in income by buying more, then maybe you can alleviate her fear of holding more debt.These are business assets, it's best to treat them as such.

The only way to do that legally on a regular basis without fear of legal issues is to become a licensed agent.