Also look into whether the city has already set up regulations around STR or whether there are potential changes coming down the line. 

Provided you are sticking to the letter and spirity of your rental agreement, you have to set boundaries People that get indignant over you setting boundaries are not worth worried about. 

What sets your lisitng apart?

You know how to manage a property.To get started, your first steps should be getting licensed then meeting with a local RE attorney so they can help you get set up with your contracts, management and lease agreements, etc.

Setting up your purchase money loan to allow better refinancing is advised when possible.

Processes have been set up to provide a degree of protection to parties  involved in subject to transactions.  

If I did set out to invest in the local area, I would scrutinize the numbers like crazy and be extremely conservative with my estimates.

That content and similar content out there sets unrealistic expectations that anyone can put together their "team" and invest in distant markets.

I am subletting a property that I am planning on purchasing the set up where instead of any type of security deposit I am re-having the property which is necessary before I rent it out.I will have about $20,000 in expenses all before I purchased the property.

I would say get connected with a local agent and also set up with a lender that has you pre approved to make it super easy making offers.