I think the easiest way is just to set up an excel file for the property and put together a punch list, room by room. 

But it turned out, it was his roommate (who moved in without telling me, but turned out to be a good tenant) that was doing the cleaning up.

Has owner financing come up in your conversations with your friend from church?

Building strong relationships and continually learning will set you up for success.

-Transfer the property into an LLC – This may allow me to take ownership while potentially avoiding property tax reassessment, however this sounds like an involved process-Establish a living trust for my aunt and mother – The trust would specify that I inherit the property upon their passing and provide step up in cost basis but i'm worried that the living trust can be modified to have me removed (who knows what can happen) - My mother is somewhat volatile.I would like to live in the property and my mother will live in her second property with her husband. 

The interior was made up of high efficiency HVAC systems, contemporary lighting, and electric water heaters.

If you have checkbook control you’ll have a bank account with a bank that has FDIC insurance up to $250k per account.  

I'm rooting for this to be wrapped up!  

The repair was extensive and costly, requiring excavation (about 3x6 feet) to replace the broken section and clean up the mess.

It's up to their tax professional on how to present that info on their tax returns.