I use the free version of stessa however there is a pid version as well. 

It works well to have more consistent income, even if it is lower than STR rates sometimes.

furnished finder for a midterm rental will probably work well.

This guy made a whole website. https://zuubly.com/invictus/ Here is the BBB complaints as well https://www.bbb.org/us/az/chan...

A mortgage company is usually an organization that only lends mortgages.  

I'm trying to stay more organized and find a more useful option.

Did a contractor walk this property with you as well?

But, for instance, someone who has lost their job, probates, someone who has been transferred, needs an immediate sale, it's been a long time on the MLS but hasn't sold, plus properties not up to MLS standards so they won’t list well on the MLS, and other of "life's occurrences" are all reasons some people sell on subject to.

I have heard this as well.  

Hey @Henry Lazerow - I would tend to agree that most of the NW side of Chicago 2-4 units don't play out perfectly well for BRRRR deals.I always looked at any potential house hack vs. having to rent - if my overall payments were less than the rent I generally considered that a win.For me...the house hack is just the ticket into the amusement park and then the fun rides come after...getting started can be overwhelming and hard so I can see why people might take a discount.I think one of the keys to strong equity creation is square footage creation which is basically what you outlined with duplexing up or down.