I am planning of making it a medium or long term rental.

The amount of time you will waste trying to dance around the issues will be legenday and shall I say, "insisting on being right (or insulted) when you don't know the answer can be costly".I was planning on getting a CPA, but not knowing the right questions to ask of someone who I don't exactly trust yet (as a new customer) isn't the best way to go about things.

I signed up for the unlimited books on tape plan and wanted to say it's fantastic.

Having an existing HELOC is always a great resource (if you are planning on repaying the HELOC through the sale of said property, assuming equity would cover the loan payoff.

I have a plan to use my 529 plan to help me get started. 

Is the plan to pay it off out right after the fixed rate expires?

If it’s allowable I’m planning to send him a cease and desist letter to get the heck off my property unless he’s using the ROW for some form of access.

This is my plan and feel free to tell me what I’m doing right or wrong.First note: i DO NOT have a **** ton of cash sitting around. 

- You missed utilities in your holding costs- For your first rehab you should plan on a little more than 6 months, just in case- You might want to double check your tax number as taxes in NY can be pretty high- The biggest area where mistakes are made for new investors when it comes to flips and BRRRRs are in the ARV and the rehab cost.

As far as managing the property: IRS rules prohibit any disqualified person to provide services to qualified plan.