I love how you’re already thinking ahead about the resale.

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. 

Maybe if worth $300k, someone will purchase at $250k.  

All content is available online and is not worth 10K.

It's worth mentioning the STR regulations are relatively new, and I think some properties currently operating are basically grand-fathered with the old permit, and I don't know if being a new owner one'd be able to get a new permit if it's not in the designated location.

Here are some details: 1) The condo is in Kona Hawaii and the three of us all live in Colorado2) According to Zillow it is worth just over a million.

You'll be selling a house that is worth what comps say it is worth. 

Our plan is to own $100 million worth of real estate by 2030 and become the premier property management business in all of Indiana.

i have seen that quadplex on the market for a while and yea it is definitely more than i would like to tackle right now but i think i could possibly make that SF work thank you for the recommendations  @Anthony Benoit For what it's worth, I'd estimate you'd need to negotiate the purchase price on that SF down a bit to make the numbers work in that area (BRRR or F/F).

It isn't worth it for them.Another interesting option is to save up and house hack locally.