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

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 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!

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. 

It’s worth shopping around and asking different lenders about their specific jumbo loan programs.Recommendations:Shop around and contact specialty mortgage brokers or credit unions in your area that might have more lenient jumbo loan programs.Ensure you have at least 12 months of reserves ready in case the lender requires it.

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.

my concern is your mention going to a feeder event.. the 3 day work shop then you have to pay the big dollars this is exactly what the gurus who are backed by fulfillment companies do.