How important is it to get with CPA to assist with tax benefits.

I believe you can benefit from his course(s).  

Renovating your personal home has several advantages that can be difficult to quantify since you experience the most benefit directly.

If this is the same person you've worked with for years and have a good working relationship I would first give them the benefit of the doubt and reach out to two other accountants to see if they will do a complimentary review of you previous tax returns.

Live where you want and invest where the numbers make the most sense.The benefit of living in NYC is that you hopefully make a nice salary compared to others in the country.This gives you a competitive advantage when you want to buy properties in other parts of the country.If you are investing in NYC, you are not investing for the cash-flow but the potential appreciation.I used to live in NYC(now I am a digital nomad) and I decided to invest in Florida.

Cheers,PatCost segregation will likely yield benefits as well 

That is the benefit to the landlord, and the disadvantage to a month to month tenant... rent can be changed at any time.  

Good property management can mitigate some risks and handle tenant issues more effectively.Ultimately, some investors are drawn to these markets because they see the unique long-term benefits as outweighing the challenges.

This way I'm semi-retired working my own hours and enjoying the tax benefits of a RE professional.

Without the income tax benefit, it really starts to feel like any other market, especially when you're not there to handle things firsthand.