An easier route would be to convince him to go in on the short term rental together in a partnership. 

A lot of people tend to mingle these things when they talk about "break even" or "cap rate", but that leads to a lot of confusion.Let's use some real numbers which may be easier to understand. 

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

It can make life easier when it comes to having to make a business decision and think with your head, rather than your heart. 

It might be easier to scale with MFU.

I'm an investor and mortgage broker and have options for loans that go as low as $75,000 and down payments as low as 15%, which makes it easier to stay above $75,000.

Since your Dad doesnt want to deal with your Aunt , what makes you think you will have it any easier . 

We take the easier ones these days. 

This is one of the things that sound a lot easier than they are actually done.The crazy thing I learned about these CA fires is that the heat radiation is hot enough (1500-2000F) that it will ignite your furniture through the windows.

DM me if it would be easier to just have a phone call and we can try to narrow down (eliminate options) so you have a 1-2 to focus on and research.