We lived in a little apartment above the garage and rented out the main portion of the house. 

I think the ultimate situation for what I described above (not the plan, but a possible outcome) could look like this:Rent main house by the rooms while constructing ADU.

We have learned so much, the main thing is that your architect matters a ton.

I'm worried about the permitting process on the front end taking too long in order to get these renovations done (mainly the fix for the foundation).

A little background: Feel free to scroll down for the main reason of this post...I started out in 2011 trying everything to make my start in real estate but was not successful until 2015 when we purchased our first duplex in Fresno CA.

Though, my main goal is to be break-even or close to it in cash flow once a property manager steps in to take over. 

Our main issue is these properties are owned in an LLC.

It would be mainly rented to alumni, parents of students and people exploring the area by the University of Florida.  

There are many articles and podcasts from BP that they talk about that.The main thing is fill you up with as many information as possible.

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).