Quote from @Gabrielle Cutler: HI there,That’s partly why I’m on here, I’m not quite sure the best route, especially living in the Bay Area where everything is a bit more expensive.

If your willing to do so, you can live in the casita and then rent out the main home and have your tenant pay the majority/all of the mortgage (depending on what type of deal you find obviously). 

I can promise you that my first deal was TERRIBLE, but I lived at a reduced monthly cost to living than renting/buying a single family and that is what mattered. 

Also, what if I can't find people to live in the home?   

Did you plan to rent this or live-in flip with the intent to sell?

Based on your question, you have two core decisions to make, and they may conflict with one another - where do you want to live, and where do you want to invest? 

I contacted him within a few hours of the listing going live and negotiated the deal by phone.

I live in the Champaign area.

We are working with our property manager getting everything ready to go- we are just a few weeks out from going live (fingers crossed).

We live in 1 unit and are considering the pros / cons of making the other 2 units either short-term rentals or long-term rentals.