Concerning the license, I've had one for a little over a year now.

Cook county has an extremely horrible eviction process due to the sheer volume of what they receive, how many state workers they are allowed to have, and people just don’t like evictions. 6) moral of the story - do whatever it takes to get the deal.

Any time I've had a concern or an issue it's difficult to get help it seems a host has to jump through hoops.

My main concern was to get credit for paying property taxes.

@Andrew Johnson That is actually a really sound, logical concern that I think is often overlooked.

Seeking out an attractive investment opportunity in NYC is extremely hard and huge entrance barrier for someone who doesn't have too much money.

The truth sign I see is, extremely low inventory in most cities everywhere in USA, that being said, huge demand and very little supply.

I have been talking to some people who brought up some concerns,  so I want to see if you guys have some insight. 

I'd be more concerned with that because if he runs out of money half way (or even less) you're going to be in a real bad spot... and likely not be able to recover anything worthwhile. 

Thanks for the response as well Paul, my concerns are not necessarily around depreciation (I’m pretty sure that buildings are depreciated over 27.5 years opposed to 20 years) or other deductions that are typical to long term rentals but rather tax guidance that dictates what is a schedule E rental portfolio vs. a schedule C business similar to hotels.