This creates a market for both short-term and long-term rental properties.Affordable housing, Compared to cities like New York, Washington D.C., or Boston, Philadelphia offers relatively affordable rent, or section 8 tenants, especially those who are relocating from more expensive areas. 

What would be a good actionable for you now is to visit open houses in areas you think you like and starting talking with Listing Agents at those homes.

If you only have a homeowners policy, and something happens like a fire or a guest gets injured, and the insurance company finds out you're renting out the house, you're in deep trouble. 

@Yooni ChoiFor a first property, $100/month in cash flow might not be ideal, but it’s acceptable, especially with a house hack.

Be careful not to violate any Fair Housing laws during this process.

I did a search on the forums and insurance seems like it could be a major problem.I have houses in two different LLC’s in Texas and insurance is not an issue at all.

That being said, if you're 23 and you don't own a home, I really do recommend starting with a house hack as you don't need the 25% down capital to get started and you kill 2 birds with one stone by getting a rental and having a roof over your head. 

I'm looking to buy a house in the St Pete market & have read zoning regulations, articles about STR (anything less than 30 days) and have discussed with my realtor.  

The house was vacant for 5 years with a new roof (5 years ago). 

In davidson county most people book an STR to be close to downtown or at least close to somewhere cool as a secondary priority (like 5 points or 12 south for example).If you have an STR in white house it's going to need to make up for location.