In that case, would the renting process be a bridge to help you retain the home for future personal use? 

But we parted ways and while it is a lot more work, I'm learning so much AND it's more satisfying to me- to have that control, end of day.I would consider working with the right PM company again in the future.

Basing insurance price on past losses does not adequately compensate for the future risk which is higher.  

Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.

Be careful about the advice of others when it comes to your RE investing future. 

The price appears competitive, and the interface seems like it might work well with adding in multiple future properties.

If you want to run your investment like a business you 100% need to establish a solid screening process that makes placing tenants in the future easier.

Yes, I realize it was the first time, that is why I would cover the cost in an effort to be a good landlord and not discourage my tenants from reporting future issues.

I would suggest giving it up and just hire an agent when you are ready to transact in the future.

I personally have been an investor in Chattanooga since 2021 and the market has shown tremendous growth and strength, and I'm super optimistic for the future.