13 Dec update:
Clayton contacted me to see if everything was going alright. This is the second time he has contacted me and each conversation has been helpful. It seems like Clayton is still trying to get his property management staff to rise to his expectations. For instance, in my most recent conversation with Clayton, he told me that both sides of my property were leased. This was great news but was a first heard for me. I immediately contacted my property manager to ask for the new lease. Evidently, the second unit was leased 12 days ago for the expected rent amount (which is great) but utilities were included(not so great). The reason this is a sticking point is that the property manager never asked me to accept a new tenant or if I was willing to pay for utilities. I now have to do some more research in the area but I am guessing that an Indianapolis winter will severely cut into the expected $650 rent for that unit (cut ROI from 16.6% to 13%).
I have two other properties, in other areas, and there is a constant conversations with the property manager when the unit is transitioning to a new tenant or undergoing maintenance (the rest of the year there is zero need for interaction, other than monthly statements).
I also received update pictures of the units and I am impressed with the interior rehab. The house is very old so the exterior of the unit (especially the front) needs some real work before it is something I could proudly show off. I also received my first payment from my first tenant at the end of Nov (4 months after purchasing the duplex).
Although things have moved slower than advertised and communication with the property manager still needs some work, I am hopeful that we are over the rough patch and I will actually start to receive some cash flow.