Last year, the city required a bank statement, which was not overly difficult for me to produce; however, this year the city of Chicago required either a homeowners exemption or a state license showing the exact address and unit for the listed AirBnB. 

Sounds like a good deal and you must be handy to have done all that work.

Can someone help advise what I'm missing? 

For experienced investors, do you see a scenario where an investor would assume the properties at a reduced rate which would allow us to cash out and them the opportunity to earn some easy money while holding the properties.For example: Say if we wait, we will sell the properties for $1M.

You can use anyone really in CA who can help out, but of course they want to see the place.

Once you know you can get a loan, then it's time to start hitting the streets and making it real.  

It also helps you build the intuition on how much you can offer.

I would use cleaning services but it's my understanding I could use more than one company over the course of the year to limit how many hours one company spends on it.I'm looking into a utilitarian STR more for business travelers, so this won't be one where everything is perfect, it's bound to accumulate wear and tear I think.The STR would be out of state, but I plan to travel there for probably two weeks a year where I would perform many repairs myself.

Pretty much whatever makes sense.My plan is for it to be a midterm rental most the year and then be there for a portion of summer to be close to my daughter.  

I should add that there's stairs to the basement which is finished and it has a big area.