I will send you a couple people to ask about the permitting. 

This business can be a bit scary for new comers!!

Would love to hear from you , to get a better sense of the numbers and challenges. to be more specific:how is working with the city in terms of inspections and permits?  

Property is protected by different types of Lease Restrictions according to zoning requirements - each subdivision is subject to both zoning requirements and developer deed restrictions - both of these can affect how long you can rent / lease a property for .There are some areas that have no restrictions at all and others that only permit owner occupancy and every variation in between really - you would check each property for their specific lease restrictions or get your Realtor to filter for it.

With the 100k you'll spend on a pool, insteqd add 2+ bedrooms (permit allowing). 

I will be submitting the first permit this week, landscape.City of Jacksonville Required Permits 1. 

It could be moot point if it is 2 years.It would be a good idea to find a lot that already has perked for the septic and has a permit.

Yes, just call the city and ask for the permit history.

Part of the reason I left LA and decided to invest in Oregon in 2018 was because of the demand for coastal vacation rentals and the openness and easiness of short term rental permits.

The most interesting quote was: "According to the Frontier Institute, a Montana-based libertarian think tank, a city like Missoula, which is still more middle class and affordable than Bozeman, has exclusionary zoning — restrictions on town homes and multifamily units, minimum lot requirements — that make it difficult for young families and working-class newcomers to get a foothold in the city.