I don’t know why we didn’t get that vital piece of info in our initial meeting.So my wife and I are extremely relieved .She says she will stay on as a courtesy and if things come up it will just be an “ hourly “ rate for emergency type situations or basic boots on the ground necessities.We really like her enthusiasm and positivity and she is great at communicating and seems  sincerely empathetic to our situation.

Some jurisdictions are taking the statewide ADU rules and going much further extreme.  

Given this is one of the rougher neighborhoods, I'm a bit concerned that the next set of renters might not be as good as this set of renters.

It also makes it harder for other operators down the road--- not your main concern but we all impact each other.What about you and your wife live in the garage unit, and rent out the house for a lot more, at least until all this permitting is figured out.

I’m not so concerned with how to turn them on, it’s more what immediate issues may I encounter when doing so and how can I mitigate them.

I did a background check and was able to look up his many properties across all states so I really don't have concerns he doesn't have any assets.

All of us have stable jobs and no other outstanding concerns.

Quote from @Kyle Deboer: Being a beginner, the only markets that I am really tapped into at the moment are all extremely mainstream (zillow, realtor, etc.) and I see everyone saying I should learn to tap into underground markets but I can't seem to find anyone explaining how...

The inefficiency of this system makes it risky to rent to tenants without stringent screening processes.Consequently, I have had to adopt extremely strict criteria when selecting tenants.

Regardless, the person with the umbrella policy has no big concern and should not lose a wink of sleep.