BUT then, the tenant complained that they were paying for the credit boosting feature in RentRedi and would not be getting their credit-benefit if the other tenant didn't pay on time. 

You might not cash flow right away, but even just offsetting what you were paying in rent while building equity, getting tax benefits, and learning how to be a landlord is a game changer.

Your property definitely has the potential to benefit from a cost segregation study.

Would either of you be willing to explain cost segregation and benefits of using it as an agent?

My return is infinite as I do not have any money stuck in these.I like the fact that there are numerous ways to make money in real estate.   

If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

The benefits that come with them can be attractive for sure.

I think there are some tax benefits that outway the small negative cash flow that you're currently experiencing. 

Central Kentucky, in particular, has benefited from Lexington's growth, with many people commuting from outside the city for work.

It will familiarize you with the basic terminology and benefits.