You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

Find one that fits with your life and how much effort/capital you have.

This one might need a house manager in a few months so some chance to live cheaper in exchange for managing the house. 

I really want to just relax and have a happy life and hope for the best.

Usually, this is a sign of stability and a preview of the types of people who live in the area. 

So even though I lost a deal and commission I won loyalty and a client for life and became very valued as an agent and very successful by getting the money that was deserved and obviously, rightfully, morally and legally due to her.  

I don't live in CA, and wasn't aware of the Prop 13 passing to the next owner if it's parent to child and both live in it as their primary.

You have the ability to sell while limiting your capital gains tax because you lived in 2 of the last 5 years. 

Just to confirm my understanding, you are living in a side by side duplex in Miami - you want to renovate the other side that you aren't living with a renovation loan?

I assume you’ve got a loan that says you will be living there.