Piggybacks were big prior to it and people got over leveraged. 

Let's rephrase something, she didn't "lose" her last month's rent, she is already BEHIND one month compared to all your other tenants.  

You'll want to get an idea what comparable properties are selling for/renting for/etc.

Once you live in it, it's still updated, but not at all compared to a flip.

What questions should be raised with the agent prior to signing? 

Sec 20:33(1) - for funds deposited at least 1 year prior and 13:3881 (D)

It was a flip, and my first investment in NY, however I have done flips in CT prior.

@Tulan Kantesaria, @Matt Motil, is right if you were in flipping business.S-Corp will do no better for tax saving compared  to LLC.  

Entities are mainly used for asset protection.However, some would argue that by structuring you will lower your chances of having an audit of your taxes due to the lower ratio of audit for entities compared to claiming it directly in your 1040.If you are using a multi members LLC taxed as a partnership, this LLC will only file an informational tax return (1065) and each member will pay the taxes on their own tax return, based on the K1 that the LLC provided them.

He bought it awhile back as a personal residence prior to joining the military, and couldn't keep up with the payments.