Also have a plan to manage your units, it is not for everyone, and Newark has its own unique set of challenges, as does any market.

I am looking at a 1957 larger duplex (1300sf/side) that has fairly decent bathroom décor in both units and one kitchen with older metal cabinets that are good but dated. 

Wow, that is unique.

If you did it it would be great to find a way to track what it actually generates like a special phone number that's only on that sign or an sms (texting) short code, special offer, code to mention etc that only that is unique to that sign.

They can use it as decorative only.

All of your comments give me a good starting point for my research and I will definitely speak with both my attorney and CPA regarding the unique implications these larger multi-families present.

There's really nothing unique about "affordable housing" or section 8.  

Offer something unique or different in your rental. 

Depending on where the condo is located, and the state of the decore and furniture, she may be able to rent it fully furnished as an executive rental.  

You bring up some good points but after looking at your BP profile  and your  LinkedIn page ( very impressive btw, we're two years apart in age), it sounds as though you're in a unique position as you  provide a service that is absolutely essential to every serious.