Have it held in escrow by the title company or an attorney.

I know not all title companies are created equal and that few will close on a deal at a certain price point or do what's necessary to clear title on messy title deals.

First time dealing with a title company.

Some credit providers charge $50, some charge $200 and you don't have control over this unfortunately.Title fees: since you are purchasing, you probably didn't choose the title company, however this can be negotiated when you submit your offer.

After some digging, I feel like the HELOC would likely be the preferred route for funding my next project.

Multiple, billion dollar companies are investing investing heavy in our area, such as Intel, Google, and Amazon.

I can provide a lot of advice as I've done several LLCs for our companies and I'm right down the road in Tampa.

Talk with a NY lawyer about your plans and preferences and they can make it happen. 

(Example dollar amount)I’d prefer SFR examples, because obviously larger apartment deals while really juicy are also at a scale I myself cannot yet reach.

I would like the listings to be similar in price across all platforms, but since they won’t be exactly to the dollar, I’d prefer Airbnb and vrbo to be the cheaper option over booking.com.