The main challenge was that there was considerable deferred maintenance.

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

That's the reason why we sign leases in person, so we can go over the main issues in person and make sure they are understood. 

Mainly because they advertise saying they have been investing over the last 15 years and been wildly successful.

We also have a bank account at a smaller Chicago community bank, but there technology isn't as good to be honest.I think @Jonathan Greene's main point is don't step over dollars to pick up pennies. 

Problem with Zillow and FB is they have this annoying "1-click reply" where people can just click on your ad without reading it and you get an automated message "Joe is interested in your apartment at 123 Main St."

Now we're seeing investors pouring money into buying Class C rentals - but, many are getting burned.In our experience & opinion, the main determinant of property Class is not location or even property condition, those are #2 and #3.

That being said the main issue with leverage is being over leveraged.

That said, my main question is, can you recommend a good mortgage brokerage company that offers all the training points you outlined in your post?

We’re moving into the ADU ourselves starting in January so we can remodel our main home.