Haven't firmed up a property manager yet, but happy to share names once I receive one. 

If you know anyone/is someone who works at a investment or property management firm in NYC, Westchester or East CT please help me get into contact. 

I believe the law firm handling this for the city has been trying to serve me papers.

A good real estate brokerage firm will not entertain or interview you if you do not have an active real estate license because those brokerages are top producing brokerage meaning those companies are buying leads with premium leads like Zillow and other sources.

I could pay a regular marketing firm to build a site, but since so many STR owners have this need, I have to imagine there's an off the shelf option rather than having a custom site built.

I'm a firm believer in "do your best, caulk the rest" and I don't think I I've used 24 tubes in my entire life, I've painted some crappy houses too.

Conduct regular inspections and communicate clearly about the rules and expectations.Handling this situation firmly but fairly can help maintain the integrity of your rental property and ensure a safe and healthy environment for all tenants.

I'm interested in lending in the Dakota's since it seems like none of the big firms are doing so and would appreciate a contact to call and learn more. 

I will have to Google it before coming to any firm conclusions.

Get a sense of the neighborhoods, comprehend the dynamics of the area, and evaluate the general investment climate.Remember that doing your research and having a firm grasp of the local real estate market are essential for successful real estate investment.