Insurance means a 3rd party may pay out.  100% different things.  

@Andrew Cowles, a very good question.In my state, and your state may differ, the upset price is an "unofficial bid" by the moving party.

Since this is our first project like this, I'd love opinions from those with more experience...do you see fatal flaws with the strategy, are we missing the boat on anything huge, etc. 

Hottest part is Northeast.

This is not always the case, particularly with sellers who have a lot of equity and can spread that out into installments.The wonderful thing about real estate is that there are a lot of different variables available to create deals that work for both parties. 

No, love, joy, companionship, trust between strangers, all around the best time I have had since I was highschool going to rave party.

The ADU will exempt you for a while from rent control due to it being a new unit as long as you owner occupy (because the OO currently excludes it as a duplex (assuming I am correct on that part - that part is irrelevant to me because I do not OO a duplex)).Good luck

It has three 100A breaker panels in the back of the home.   3rd party inspector noted knob and tube in the attic and highlighted it's risks. 

Come on down and join the party.

If you are operating as the PM for your properties or others, this is a good coverage to have.  3)  Hired & Non-owned Auto and Workers Compensation are good to have if you are acting as your own PM and directing 3rd party handyman, contractors and vendors on and off your property.