I personally love when I get a buyer on my listing without an agent - if their offer isn't a lowball it's often times higher than what the seller is willing to do and I get a bigger commission.

I would call the city/town and ask general questions...wouldn't tell them you own some non-permitted ADUs.Find and attend some real estate networking events; maybe you'll meet another person who has dealt with this kind of situation.If you have the funds, you may want to talk with a local real estate attorney and see what they advise. 

For me personally, I find a tremendous amount of value in going through programs that help me learn at a much faster rate then what I could on my own as well as help me mitigate risk/self doubt.

Your rental property coverage is NOT going to cover tenants personal property. 

I personally own horses and it's an insurance nightmare most of the time - especially with renting out stalls to non-owners. 

I don't blame the person giving the estimate as he too will get some portions of the work done from someone else.

If he did not meet the background check to be a renter that person cannot stay there. 

Does the company have a maintenance person that will handle small repairs or will you become responsible for every hole punched in a wall or other thing that gets broken and damaged.

You could try your hand at one of the numerous online services that advertise this stuff but I've found it better to start the relationship early with an actual person as opposed to a faceless online service. 

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