Starting all over from scratch... my gray hair is turning back black....LOL.   

I did the right thing by asking for the security deposit and first month of rent before handing the keys.For the next two months, she has been a nightmare.

In 2020, we just had a property turn. 

If you’d like, I’d be happy to connect and help you navigate the Indianapolis market as you move forward.Good luck—I’m excited to see where your journey takes you!

Hey Deirdre,To address your questions:Providing freedom by handling day-to-day operations.Offering peace of mind through proactive maintenance and tenant communication.Reducing risks by staying ahead of legal requirements, tenant screening, and dispute resolution.Enhancing the bottom line by identifying cost-saving opportunities while ensuring tenant satisfaction to reduce turnover.Is the experience still important when the property thrives financially?

I navigate through cities and towns, identifying areas that are both friendly and challenging for STRs.

I suspect the person who originally turned it into a fiveplex only applied for permits to make a fourplex and then did the 5th unit fly by night (perhaps at a later date) in order so the property would still be considered residential and allow for better financing possibilities.

Ambulance chasing attorneys know their way around and can legally navigate around Insurance Policies.

Some good advice above- it really depends on their "need" for the cash.They could always turn it in to an investment property and eventually do a 1031, leaving a legacy for their kids some day. 

By this point, they will have already thought about what might happen if you leave, including the need to turn over the unit and find a new renter.