I don't think there's any state or city regulations but it's strictly between you and the property management company.

You may also want to consider any local regulations or restrictions on short term rentals, as these can vary by city and state.In addition to demand and regulations, it's important to carefully evaluate the financial viability of any potential investment.

., but even I would be very wary about pursuing a deal as advanced as the one you describe (because it would require a LOT of expertise that I don't have).Do you have a lot of expertise in real estate and business contracts, investment contracts and syndication, RE law, and local/state zoning and business regulations? 

This way, we continue to have cash flow coming in, and if we happen to have a bad contractor or one or two units and/or some permit/regulation related issues, the scale of the damage won't be too overwhelming. 

Now beginning to see municipalities regulate as in, requiring wholesalers to get licensed, I can't help but wonder what lines were crossed, who lost their life savings for that to happen.Think of real estate as an eco-cycle.

Many of these markets had vacation rentals long before airbnb so risk of regulation is low, and demand should continue to be strong as more Americans migrate to the south for employment and housing opportunity. 

The rules and regulations make using IRAs procedurally painful (to me). 

Not to take anything away from you, but you know the prices of real estate (especially in NY), so I know it may not seem like much, but I think you've overcome the most difficult obstacle and that is going from 0-1.The way I see NY is that it does not meet any basic requirements for investing: it has low cap rates, high taxes, stagnant or decreasing population, anti-landlord laws/sentiment, rules & regulations etc, etc.

I am learning about SEC rules and regulations.

Cities and towns have become more strict with second egresses.