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. 

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

Lots of headwinds facing real estate, like the following: Inflation Consumer Debt Lack of consumer liquidity-- renters don’t have first and last month’s rent, let alone a down payment to buyOwners interest-rate lockedOversupply of class A multifamilyStagnation of rent growth on assets aggressively underwritten at acquisition Maturation of term debt combined with stagnant rent growth against a backdrop of rising debt rates =investors unable to meet basic debt coverage service ratios on refinance Market normalization forcing operators and investors to rely on market fundamentals (recently) forsaken, while prioritizing expediency of deploying capitalInstitutional and local investors are both frozen by volatility and cost of capital and debtAll that being said, we feel good about B and C class assets we focus on and the markets we are in. let's connect soon 

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.