Also, What are some key probing questions I should ask the seller to make sure I leave with all the necessary information to make an educated, smart decision as to invest or not. 

During these exciting times, I'm trying my best to remain patient and do this the smart way.

I was hoping to get advice on which type of property and borough is a smart financial move.  

You will definitely want to get smart before diving in.

One helpful site I've come across is called Smart Asset and they have a property tax calculator that will help estimate property taxes. 

Using maximum leverage is not smart just because it’s possible.

. :) You can do it at the individual device level, and track connected devices and all that.

Then when you scale up to 100 units, the work is actually LESS because a 100-unit apartment complex can afford a full time property manager and a semi-full time maintenance manager. 90% of the drama is gone and all you do is manage the property manager and ensure you increase its value through smart capex.

@Gerich FellermannIt's hard to do tax planning without looking at your return but I'll throw this out there:Income taxes are lower than they have been in decades.We're likely to be in a higher tax situation sometime in the futureYour income is lower than usual since you're starting a new businessMaybe paying the tax now at a relatively low marginal rate is actually the smart tax plan?

The VA loan option mentioned here may be a smart bet.