At that point, I needed help and hired an accountant.

Beyond that I'm an insurance professional and provide insurance not legal advice.

I would suggest getting with a tax professional to assist you since there's a lot of variability depending on your specific situation not only on a federal level, but with state reporting as well.

Sounds like its time to hire a bookkeeper!

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Luxely is geared toward social media content and strategy, mostly from an RE professional (realtor, mlo, etc) perspective.

For example, if you dedicate enough time to real estate businesses and real property trades, you may qualify for the real estate professional tax status which is potentially a great way to reduce high W2 taxes. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

“Real estate professional” status has no effect on this.

Although I haven't officially hired anyone and I'm still doing my due diligence, I’ve interviewed 2 potential property management companies thus far: Harvey Property Management Group and LIV Indy.I’ll start with @Harvey Levin .