I've been reading a lot to understand where to start in my investing journey and I felt unsure why I was so uneasy with this deal, thank you for the gut check.to answer your questions:1.

Trust your gut and focus on building genuine relationships first.

I have recently been gifted my great grandparents home and it's going to be a complete gut and renovate costing approximately 150k.

You will know best by your vetting and gut with whom you could live.

Go with your gut.

I wouldn’t mind the tri state. as for the light cosmetic that just means not a full gut job.

Quote from @Bryant Brislin: Land in the path of development that may seem a little far out, but your gut/intution and common sense from an urban planning perspective tells you that some day, whether it's in 10 years, 20 years, etc it will be a great long-term position for your family to have and hopefully sell at a signifcant multiple return compared to what you've paid for it.

By renovating the entire house, gutting everything, fully renovating the pool, and with approved ADU plans.

Follow your gut feeling and keep looking for other applicants.

Sounds like their combined income likely beats your other tenants.Your gut is probably your best bet and you need to go with it.