Great question - when you find out let me know as we are looking for one as well. 

Be sure to explore all around the forums as well as many of the FREE tools that Bigger Pockets provides.I am on the lending side of things and am always happy to hop on a call to discuss loan options that are out there, even if not offered by my resources. 

I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

Many of them become entitled and create problems, particularly for amateur landlords that don't know how to manage well. 

Also Texas came out with some very strong laws on lease options as well, that is well documented. 

At some point if you're doing well, maybe turn the first one into STR or LTR, and do it again.   

Quote from @Don Bessette: I have a 30 plus year tenant that can not keep up with maintaining their unit, it is filthy inside and in desperate need of renovation, all systems are in good repair and I respond very quickly when issues are brought to my attention.It is also well below market rent, and they struggle to pay the current rate.Looking for suggestions on how to gently proceed with the notification to move. 

I would confirm this with someone a little more well versed in NYC or give them a call to see if they can answer your questions.

Hope all is well.

I think they can go very well if done right or poorly if not, and right.Here or a couple of suggestions.