And of course it ebbs and flows with how the economy is doing.. when mortgage money is easy and cash buyers are plentiful there is less reason for a seller to take back a note on the sale of their asset..  

In the current economy with low interest rates, low inventory and high demand, getting that great deal is just that must harder. 

As for passive you can look at it from a scalability , economies of scale once you have scalability and responsibility perspective.

I don't know the economy like you do nor the red flag areas to shy away from. 

They will also shrink your line of credit if the economy turns or if they feel that they are not as secure as they once were.

As far as regulations go if it’s a true vacation rental designation most of those local economies are going to be set up to welcome that and be happy to take the tax money.

(Cannon AFB) For four years I had two roommates whose rent payments funded 95% of my mortgage.In 2016 I PCS'd to Florida and I've had my house rented out with a property manager since then.Clovis, NM is a smaller area that has a lot of it's economy being supported by the base.

During a strong economy people have more money to spend so more people move into more expensive living such as single family homes (buying or renting).

The city I'll be moving into (Columbia) has a great economy and decent taxes overall (as well as lots of places for me to hike as well as parks to enjoy) and when I look at multi-family appreciation (in 2-4 unit properties as that's what I was looking at - though there are very few 3-4 units in CoMO) it's not much of a difference the past five years or so. 

For me, the components of the decision should be your local (NYC area) and state (NY) economy (look at hard data), the political environment (biz friendly or ?)