I would add this - what are your life goals?

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

Regarding the Zelle versus Avail issue, I would advise choosing your battles wisely - as with many aspects of life.

At some point, the juice isn't worth the squeeze for us and we just want to enjoy life. 

Commercial is a totally different ball game than residential, so connecting with a commercial broker will definitely make your life easier.

My family has invested here my whole life and its been very good to us. 

Let’s break it down and explore how you might approach this idea, the challenges you could face, and ways to structure a deal that could work for both you and the landlord.Why the Landlord Might Be Open to SellingThey’ve moved out of state for health reasons and don’t have family nearby anymore, which might reduce their emotional attachment to the property.The idea of simplifying their life and pursuing something like sailing around the world suggests they could be open to letting go of the property if it helps them achieve their goals.With significant equity or potentially owning the property outright, selling could provide them with a substantial cash windfall to fund their future plans.However, their belongings on the property could signal hesitation to let go or simply a logistical barrier they haven’t addressed yet.

The tenant laws in New York make life as a property owner way harder. 

My mom is nearing the end of her life and has left me and my two brothers her condo in Hawaii.

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.