As an update, my thoughts are this: Stessa is not designed to track investments, calculate ROI or CoCR, rather, it is designed to track single cash-based transactions for a property. Therefore, it does not delineate between personal cash and property cash.
For example, I have a property that I just acquired with zero tenants. Since I have acquired the property, I have replaced locks, paid for utility transfers and usage, and covered the cost of miscellaneous repairs. I am paying for these costs out of a personal checking account because I am not generating any income from this property. This account is not linked to Stessa, and I do not want it to be linked.
Since I want to track these costs (expenses) against the property, I must add a transaction to record the expense. On the reports, Stessa will reflect these costs as operating expenses, which is correct. However, as I mentioned above, Stessa only tracks cash-based transactions, therefore, Stessa will show that my property is generating negative net cash flow (no income - expenses = negative cash flow). That is not necessarily correct. As the owner, I am pumping more money (investing) into the property to cover working capital needs.
I should be able to record those expenses as contributions; however, I do not think Stessa supports that at this time.