So again, brokers will talk up about how you can get more rent, but in reality you can't, even with updates, because more tenants are want the cheapest rent for decent place.  

She would fight with her boyfriend and customers on the sidewalk in front of my house.

You should assume arms length sale in the sale/exit assumption and in this price point expect in addition to broker fees to be some repair concessions and likely even a seller assist. 

I was an electrician for over 20 years with my last electrical job being shop foreman for a custom electrical control panel shop and UL 508 specialist.

This might be a question for our insurance broker/future attorney, but wouldn't the LLC be formed in Indiana since the rental property is located there (versus Illinois where we will be living)?

That's it, but a) print out a page for each property you think is comparable, b) make the list of repairs long and inclusive of everything you've done. c) Put larger items first like kitchen remodel......and don't just say 'kitchen remodel', list things like 'custom backsplash tile/Bosch appliances/recessed can lighting/pot filler/etc. d) Cite the price/value of the work done, and don't be afraid to be generous.

I'm a licensed mortgage broker and have closed loans with clients out of the country.

When I worked as an MHP broker, if the park was on a lagoon, I could never find a buyer no matter how low the price got. 

Find a mortgage broker who will help you with thisGino

It’s a good idea to speak directly with an insurance agent who understands multi-unit properties to customize coverage for your specific situation.