Something has to get better in that market as the regulations are too confining and essentially up to interpretation by the city explore you engage with.

If we become heavily restricted, what chance does the rest of the DMV have to get their own regulations that make sense?

Hopefully this helps....You need an attorney that specializes in SEC regulations to create your PPM. 

.- Insurance Requirement: Flood zones still matter for federal regulations.

Personally, after working with numerous property managers in Las Vegas, I only trust two to handle this task for my properties.Compliance Is ComplicatedProperty management involves navigating a maze of city, state, and federal regulations.

I am not familiar with NY regulations, but investigate whether you can charge each tenant ~$80/mo for the gas (do the math).

As with most municipalities and jurisdictions, the evolution of the AirBnB market has spawned regulation and restrictions on where, when and how a STR can operate.

It's important to stay informed about developments in the areas you're considering, as well as any potential changes in regulations or economic conditions.

I also doubt very seriously that any brokerage/custodian is going to allow this kind of loan with 401k assets; it's likely going to need to be a 401k general purpose loan, which is highly regulated (as someone else mentioned). 

Airbnb properties can be hit or miss depending on location, seasonality, and regulations.