For example, If your GC tells you he will have the job completed in 1 month, every day he goes beyond that deadline (besides for "unforeseen" circumstances beyond the contractor's control such as weather and permitting) can be an additional $250 credit off your original agreed amount.  

But I'll be looking to buy more later and definitely keeping an eye out for pre built ADUs since my ADU that's being built now at my first home took 12 months to permit.

Our biggest concern is not really understanding the NOO STR regulations/permitting in the area and access to cleaners. 

I know that in Miami you have to be careful of the neighborhoods where it's not allowed and you have to get the permit to do it plus yearly inspections, but is there anything else I'm missing here that makes it impossibly complicated?

The biggest challenge was getting the utilities turned on, as I needed to get the city developer involved in pulling permits and getting the property certified.

Plus, the county of San Bernardino has put a 45 day hold on issuing new STR permits   

Depending on the market you're investing in you may have permit/license application fees before you can start renting.

The city is good at issuing STR permits.

Detached homes have to renew their STR permit every two years.

Do you see permits pulled on the city website to support the deconstruction?