One thing to take note of is that a lot of places that are established STR markets have regulations stating that you have to honor future bookings.

Are there any rules, laws, or regulations regarding this?

Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed. 

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

Seacoast NH, for example, has some great potential with short-term rental markets (Airbnb, VRBO), especially in towns like Portsmouth or Hampton, but the regulations can be a bit tricky.

Make sure you thoroughly know how the regulators view the way things are being done, before committing to a "creative financing" technique.

Having developed a majority of my career in CA the regulations and red tape for construction and development are intense. 

A good property manager can help with tenant screening, enforce lease terms, and handle evictions more efficiently if it comes to that.Require a Larger Security Deposit: Within the bounds of local regulations, a larger deposit can provide a cushion in case of damage or unpaid rent.Consider Rent Guarantee Insurance: Some companies offer insurance products that can cover lost rent in case of tenant default.

membership is something like APPL which is just non regulated group of private investors working on best practices but there is no authority behind them like  state license or NMLS registration has ..

It is a federal regulation but some states reach out and screw you.