Quote from @April Rae: It sounds like you’re dealing with a tough situation, but there are steps you can take to resolve it while maintaining a positive environment for your other tenants.

It has not been well maintained over the last 19 years with a string of just bad renters and the person I had managing it just didn't do good quality repairs or work to it. 

You get an exponentially better opportunity & reason to invest.Now, there will be headwinds-- climate change, physical capex to maintain physical structures,human beings, etc.

You might also consider maintaining a certain level of cash reserves to handle maintenance/capex as needed.The general point the author is emphasizing is that to reap the benefits of compounding you must reallocate your cash flows into the same or other cash flowing investments rather than spending them on discretionary expenses.

Are there any best practices for maintaining accurate financial records and documentation for these transactions?

All said, I am not coming out much ahead for a property I have owned for 20+ years and had the hassle and expense of maintaining.

Just wanted to know if anyone had a non excel sheet based automated solution for collecting and maintaining COIs.

They may feel a sense of entitlement, and they may not even be good renters.Unless this is some unique situation like a ranch that requires special skills to maintain the property, I recommend you remove the caretaker, spruce the place up, and put it on the market at market rates.I also recommend you look for a professional property manager that can help you navigate this immediately.

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