My advice would be for sure to become a part of the FB group Short Term Rental Listing Advice through the Short Term Shop, Also become a part of the STS community and ask questions there and you will get a boost!

That seems like a lot and I'd like to shop around -- can someone recommend an insurance agent or broker in Chicago?

Currently shopping around for a convention loan for first home to house hack.

A lot of borrowers shop lenders for days to find the "lowest rates" just to find out 3 weeks later that the lender cannot perform on their promise.

Get a strong shop vac with bristle brush and carefully clean off the condensing unit. 

So they'll help you pick the finishes and hand you a shopping list and then you do the rest DIY.

My father studied to become a plumber and my mother worked in a dry cleaning shop.

Plus stick with our lenders and don’t shop rates.  

She can work at one of the big companies here in town for some experience or set up shop on her own. 

Additionally if you can live in one unit for a year, then you can get the best of both worlds, better financing and a larger than a single family home. 2-4 is a great place to start, shop around for pricing and see what is available.