I’m continuing to work with the tenant, but we’ll be approaching two weeks late with no signs of plans to pay.

Determine at what percentage of completion you'll pay for work done. i.e.

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

Or you could pay cash now and refi later.

Now, you need to figure out how to find deals and pay for them.

Owning a duplex at 20 is a huge accomplishment, and it’s inspiring to see you’re already planning your next move.From my perspective, real estate investing is a long-term game focused on building equity, paying down debt, and maintaining stability over chasing short-term cash flow.

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

We can still choose how much to pay someone to operate it if necessary.

Be patient, it's going to pay off. 

I could say a particular town or area, but if there aren't any, many properties for sale that doesn't help.