BTW2, I generally advise NOT investing out of state ... been there, done that, and it was very painful for me; your mileage may vary.

This month - facing four vacancies, semi-annual property tax bills (most of my mortgages are commercial and not paid through impounds), insurance renewals, a new garage door and repair bills (when it rains it pours) for plumbers, I am glad I passed on that last duplex for now.Although it's always painful having to stroke large checks multiple times in the same month, I'm glad my reserve is there.  

Maybe he needs more pain before getting the price down...if so, move on.

Man @Kurt BrumfieldThere is pain with family and friends!

Base part of your analysis on the leases(I'm assuming those have been provided to you,) verify that the leases are essentially market rent- if they are under, you're actually in luck as you'll have future upside, and you can factor the below market rent into your purchase offer- and if they're over, that may signal that some desperate tenants signed leases that they'll break at the first opportunity.

It's kind of a pain to break everything up, and run and keep up with multiple depreciation schedules on each property and don't forget you have to recapture your depreciation when you sell the property at ordinary income rates witch may kick you into a higher bracket on the sell on the back end costing you more and total tax, so you need to consider your exit strategy.  

The city is a pain in the ***, but manageable.

Curious on everyone's thoughts on this and if there are any options or is this is clear signal to RUN AWAY!!!!

So we're supposed to find out details about what's going on in their life circumstance, what their true pain point is for selling their house.

@Phylicia Stephenson - Welcome to the vibrant BP community and as a New Yorker sharing adjoining counties.I see that you are interested in duplex acquisition for house hacking and flips, so, I added two blogs for your review.http://www.biggerpockets.com/renewsblog/2014/07/19/how-to-buy-a-duplex/http://www.biggerpockets.com/renewsblog/2014/01/07/flipping-houses/On the other hand, I share your pain with regard to the high price of properties and taxes that you encounter in Nassau county.Yes, you will probably have to step out of your comfort zone in Nassau county and look upstate as mentioned.