Congratulations for making a decision.

During both work orders, we dispatched a licensed and insured plumber. 

Does anyone know of any good insurance brokers as well ?

However, many lenders and insurance companies are tightening restrictions and premiums for these types of properties.

Absolutely use their payment processor and insurance and don't allow cancellations.

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

The podcast also talked about insurance claim re-housing where families lose their homes to a tragedy and get replaced through their insurance.

Yes you have insurance, but it may not cover everything.

unless or until an investor understands and can somehow quantify risk in each investment they’re considering they can not make a proper investment decision.  

Hence, the decision was to make the flight using a single-engine plane.The same logic applies to multi-family properties: a fourplex has four times the vacancy risk of a single-family.