So, while my research did not find any rental restrictions for STRs I did not discover that they couldn't give me a business license (before we bought the house.)After talking with the City Planner about the situation he told me I could go through the same process that a hotel or B&B does (approval process for Certificate of Conditional Use) but it basically comes down to a City Council meeting which is a public hearing.We discussed the fact that there already were people operating STRs in the city (and obviously not paying taxes to the city since they would not have a business license). 

There are a lot of financial planners out there who will tell you to pay off student loan debt before investing in RE.

Hello Justin, I'm not a property manager, I'm just a newbie (looking for my first duplex, triplex, quadplex) who happens to be a planner, but I do have local area knowledge.

Seeking references for site planners and architects to consult with. 

Then meet with the city planner and describe to him what you would like to do.  

I was a City Planner in the late 1990's for a municipality in Central Florida, and a Land Planner / Consultant for developers in the first decade of the 2000's. 

Call lenders local to the property until you encounter one that can spell "continuity of obligation" without the use of a spell checker.Talk to an estate planner, too.

@Scott Trench  Well anyone who says you can get by on little sleep because the need for sleep is a sociatal delusion, and uses his book as a platform to sell daily planners and calming aura and soothing chakra tea,  isn't someone I'd look to for serious life advice.

One that is on a first name basis with every City planner.

OK then instead of grazing cows you can graze lama's ... in the states you could hire a land planner that would walk you through entitlements..