I did a search on the forums and insurance seems like it could be a major problem.Shouldn't be an issue at all. 

As a sole operator, you have all the policies and procedures in your head and can apply them to many properties without referring to a binder.

This happens all the time, usually with heirs, but it can be squatters as well.

All that cost's $ in labor time and systems.     

Not at all looking to stay strictly in the NYC area; have been looking around at markets in Long Island, Upstate New York, New Jersey, and the surrounding region.

Quote from @Somesh Mukherjee: Hi all, I am looking to diversify & add a small apartment (3-4 units) to my portfolio.

You lose all of the control and these are long term investments - but in my experience the returns match what I had on the active real estate and I am hiring professionals to manage the assets.  

Hello all!

Aloha @Kory Sheldahl -  yes, you can all his commanding officer. 

Even if one has to provide the education to some of the parties as to why a particular creative solution makes a win-win-win for all.