If you want to take the time to learn the investment, deal with the hassle of the day to today, and keeping up with the regulations then go for it. 

We need fewer regulations (or at least the correct ones) to incentivize housing construction and more up-zoning in appropriate areas to add density to existing lots.

If you wants to find a property in Nashville you should define your investment goals, research the market, choose a location, assess your budget and financing options, choose a particular type of property, become acquainted with local regulations, network with professionals, conduct thorough property search and due diligence, think about one’s long-term investment strategy and assess risks and opportunities.You can locate a good home in Nashville by taking these steps and consulting with knowledgeable local consultants.Good luck!

What is the regulation environment? 

You should also familiarize yourself with landlord-tenant laws and regulations specific to the market you choose.

Research the local regulations.

I've reached out to the City of Winston-Salem to gain more information on tiny house regulations since there was not much to be found online.Thanks!

Lenders face far more regulations when lending on owner occupied properties which may limit your options.

Hi Jacob,I agree with Bruce, if you can show up or call the HOA to find out their stance on 30 day rentals this would help you figure things out better.Ask to see the HOA's Bylaws and CC&RRs (Combined Community Rules & Regulations) to see if there is language that allows rentals/leasing (without restriction).If there is, determine what the criteria is for amendment changes to the CC&RRs.

Definitely look into STR regulations in any area you're researching.