I have fired customers because of their attitude , there is no law or regulation saying you Have to work for someone .

Cons might include increased inspections and regulations, potential for property damage, and the possibility of dealing with tenants who have more complex needs.

But each succesive year since the early 2000s have seen numerous rulings around the periphery of this issue, especially with trusts and similar entity law. 

With all the new regulations and liability, I'm not seeing the same kind of reckless appraising that drove the lead up to the bust.Jay mentioned having cash reserves to weather problems.  

How local governments regulate STRs will determine a lot about the area.

Here's a first...Throughout the year's I've ran numbers on numerous properties, single-family and multi-family.

The regulations are significant.

Virginia Beach offers numerous investment opportunities, both in-state and out-of-state.

There are 5 counties, one incorporated city (SLT) around Tahoe and 2 states Each county has it's own STR regulations.

Lot of great replies on here already - only thing that I would add to consider is getting a few outside opinions from realtors, other hosts, property managers, etc. about the medium to long term outlook for STR regulation in your specific area.