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!

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.

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.

@Rich Riesmeyer  You could probably use the cement board but it's a pain to install and it's really difficult to make it look good.  

I own/manage properties in Riverside and I consider that a pain sometimes...even though it is only an hour away.4) I'm with Jon in that you could consider doing a cash out refi if that is an option.  

The "practicality" of this endeavor will be dependent on your hunger to find those off-market properties!