I thought about calling rentals but my fear was that I’d just reach the property managers instead. 

Another pro can be that neither accountant will likely increase the bill to you from year to year in fear that the other accountant can steal the business.

I don't want to pay the contractors 100% upfront before repairs are completed due to fear that repairs will take a long time and not be a priority since they have been paid upfront. 

i have been listening for the last 8 months and think i have overcome my fears but have some problems.

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. 

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.