With that said, there is a constant threat of a change in regulation, and my Palm Desert property will have it's short term license taken away at the end of 2019 (along with all R1 licenses) if the laws stay as they stand. 

Always best not to invite further government regulation and interference into your business anyways.  

Each state has different regulations on how rents, security deposits and past months rents are to be handled.

Once you receive the deposit from your tenants, make sure you keep that money as restricted cash in your financial statement.It is ok to be in your bank account with other cash as long as your state regulation allows but you should properly keep it separate on your book to properly record it in terms of accounting.  

Private money is a very niche area that has fairly constantly changing regulations.

As far as vacation rentals in Las Vegas - those are largely illegal now and if not illegal, very regulated. 

Dig in to the data, look at the occupancy, average daily rate, seasonality, regulations, etc.

(totally fixable,  but see point 1)5)   Increasingly complex, risky, and punitive seattle rental regulation ordinances already on the books6)   Winter Rent Control is coming.   

If you do not take ownership of it and try and broker / wholesale it, a Note by the SEC is a security instrument and may be very similar to a stock, so in order to broker it you need to be licensedI do not know anyone who has ever had a complaint or been slapped by a financial regulator for this but if you talk to an attorney most will take the cautious route and say brokering without a license is a violation

I've been passively looking at commerical opportunities on cape cod but this market is extremely challenging with an much regulation, historic preservation, flood zoning and septic issues.