Perhaps there is a relevant book or podcast that you could suggest to expand my knowledge in this area.Considering you're experience with creative finance deals, which you mentioned previously, I am keen to hear about your personal insights and experiences.

The downside will have more to do with your business personality.

Personally, my primary residence has appreciated around 6% in market value and I live in Levittown. 

Did you end up flying and looking in person in the area?

Personal finance is as much behavioral as it is math.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

Personally, it’s something I always expect from a short-term rental, and it can have a huge impact on your reviews.To make things easier for both you and your guests, consider smart tools like locks, outdoor cameras, and smart thermostats.

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Yea this is a long-term personal play more than a strict STR deal. 

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.