We are taking everything into consideration before moving forward and Bigger Pockets so far has been EXTREMELY helpful. 

Really disappointed on those ones because it's a turn key!

With extremely high property taxes, unfriendly landlord laws, and expensive housing, I think investing somewhere else makes sense.

One of my projects, I hired a contractor who handled almost everything after the plans were approved, and I have also done a few others where I was extremely hands on.

Unless you know a licensed contractor extremely well, have supplies already or decide to explore alternative methods for getting it done, my guess is your renovation expenses will be well north of 40k. 

Most lenders won’t do it and the ones that do will charge extremely high rates.

As Calvin already mentioned, they're extremely low compared to Westchester.

I flat out told him a 200% markup for a bathtub and surround seems extremely out of the norm.

Every person is unique and different and unless you hold securities licenses or are a CPA, I would remain extremely broad.

The majority of properties that are zoned for STRs with city codes, are sold extremely quickly and are usually 'off market' properties.