Another thing to add is the regulations, HOAs and Cities are imposing a lot of regulation on short-term rentals or rent by a room, I have seen some HOAs regulate the amount of people authorized to rent the property too.It requires to do a lot of due dilligence to begin with mainly in such big house. 

They snuck under the rules by claiming that private individuals had the right to offer other private individuals the service.So again, how do these cities get away with regulating people's abilities to rent their homes on a short term basis? 

Also check if there are any boarding house regulations in your area that would impact you. 

Also, factor in local regulations, HOA rules, and seasonality, as STR markets fluctuate.

Quote from @Cameron Masters: In my experience, cities are going to be much harder than working in unincorporated cities within the state that only follow county regulations.

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

And the laws and regulations here are very different, not very strict like the states.Prices are high and rents are low over here.

Hello everyone! I'm a 26 year old from Long Island hoping to acquire my first rental property by the end of the year. I do pretty decent for my age, and I live at home still, so I've been saving up a lot of money. Sad...

I attempted to engage in professional discussions with you on here when I did work for RADD and represented them (Dutch) in a professional manner, you had no desire to do so other than to continue to post.   

@Tara JosbergerCharleston is a strong market for real estate, but local regulations play a big role in investment strategy.