I typically can get a property manager for 8% in my area but I'm guessing 10% isn't bad.  

You typically get one or the other.

With architect/engineer drawings, it is black and white.  

Typically you have a line that says you or someone you work with or someone you find will buy the property.  

From the outside it looks like a typical 2 ded 1 bath 4 plex( 2 doors up stairs, 2 doors down stairs, 4 kitchen, etc). 

What is the typical expense rate in the area?

First world problems.I don't think the 2% rule is a typically achievable goal anymore.

Is this not something title companies can typically wrap into closing due to the length of time it takes to complete?

@Raul R.I am not an expert in short-term rental rules in NYC.My understanding is that it can only be deemed legal if the host does it in an apartment that is deemed commercial and below 4 stories.With that - I take it that anyone doing a STR in a building 4 stories or more is illegal.Furthermore - people who are doing a STR in a building 4 stories or less where the building is not deemed commercial - then it is illegal.A lot of people are playing outside those white lines.

(I know @Jeff White actually bought a fourplex in Villa Park, but for more than your price.