I recommend talking to a ranger about their maintenance as it may be more involved than you think.

If so, i bet they would like to continue to earn your business via new acquisition purchase commissions.

@Cody EvansI would say your next play depends on how involved you want to be and what your strategy is.

A structural engineer would be your best bet to have a look. 

., Arms length to avoid a step transaction would involve retail sales which would cause a recognition of gain anyway. 

I have been searching for properties in the boroughs but have decided our best bet would be to start searching in Jersey (perferably close to midtown) as properties in Jersey seem to be less expensive for a 3-4 multi family house.

Completing this form is very tricky, and I highly recommend you leave it to a tax professional who has done it before.Yes, there is some audit risk involved, but not much more than your usual risk of simply being in business.

Maybe asking about the time involved and legal fees so far can help set the frame of my offers.

I understand there are risks involved and being a landlord is a full time job; but what I wanted to know is if it's as bad as naysayers say it is.My dad thinks I should do it and said he wishes he did that when he was young.

Once you move past the owner occupied I would say is when the game changes and you will be looking for a bank that will lend more on the property and risks involved beings it will be a true investment from the banks perspective.