As that will at least help folks that you reach out to know that you are a real person, with a picture and professional bio.

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. 

Happy to chat about my personal experience if you have any questions!

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.

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. 

Would like to connect with an experienced attorney. 

If you're an experienced real estate investor living in or around Springfield, IL, I'm looking for someone to provide advice and constructive criticism of my ideas, plans, research, and goals with.