My biggest issue is that I’m using personal funds as owner contributions to these accounts and money moves from account to account on a consistent basis, so I’m trying to be diligent in proper accounting. 

It can be good to let the cashflow build up a little bit to have a nest egg.

You fail that test as well. 

I would be cautious with Lorain, I don't know that area as well, but there is a high rate of crime in that area. 

A cost segregation study looks at the overall building that you purchased and breaks it down as much as possible.The purpose of this is to increase the depreciation expense.Without a cost segregation study, you are depreciating the property over two items(Building and Land).However, a cost segregation study might identify items such as fencing which might be eligible to be depreciated over 15 years instead of 27.5 years.Depending on the year that the building was placed into service, you might be able to take bonus depreciation on certain items.The follow-up question to ask your CPA is will the cost segregation study help me, and by how much?

In this case you are the customer so it's even easier.Knowing you, I'm sure that you got everything above in writing, so you will be fine.

There's plenty of cash-buyers looking to be added to wholesaler's lists! 

The sqft seems to be the same - it just went from a 2/2 to a 3/1.  

Repairing well $16000.

I think your biggest concern would be the pre-payment penalty that comes with most DSCR loans.