Instead of throwing your deal out to a bunch of strangers on the internet, I recommend you do your research to find a local expert with 20+ ACTIVE years in real estate in your market.

I recommend people doing a side gig on what they specialize in.I am an accountant and when I worked within large public accounting firms, I had a side gig of bieng an accountant.I had a salary with my employer so regardless of how much more hours I put with them, i would be paid the same. 

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

What rent collection software do you recommend and why?

I recommend starting by contacting the county’s property tax office to determine if they are open to discussing or reviewing an appeal for property taxes.

I am closing on my 1st rental (Duplex) next week & I am going to self-manage the property. Since I only have these 2 units for now I was thinking of using one of the free websites (Cozy, Tenant cloud, etc...). I ...

An attorney recommended to drop it.

Recommend:1) Speaking with a landlord-tenant attorney about your options2) Keeping an eye on the property -> ask your old neighbors to do so if you are too far away.3) Try to do a surprise visit to catch who else may be staying there.

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

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.