If you need any assistance on areas to focus on in these two markets I'd be happy to help!

Our laws require us to offer a rental first come first served (first completed application that qualifies must be offered the unit).

Beginning your real estate investing journey with a 2-4 unit property is a great way to get started.

I decided to look into an official duplex or triplex putting 150K down that has value add with renovations and potential unit add but it wont have as much equity because it will be an on market deal. 

The landlord should be named on the tenant's insurance policy for additional protection and to assist with tracking compliance.

If I had to guess I would say your money could “develop” 1-2 houses in Staten Island but in the right market you could easily get up to 12 or possibly more good units fully paid for.

Like deferred maintenance, (bad roof, worn out water heater/AC Unit, warped flooring, water damage) etc, unpaid utilities,  unpaid taxes, a second loan, unpaid HOA fees, a bad pool, bad reputation, sometimes squatters, sometimes they were drug houses, and so on.

For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).

When I ask for an income report, I received a spreadsheet with multiple units. 

I plan to live in the multi-family for a year then move out and rent the unit.