I'm assuming the insurance company wants to pay put the least amount possible.

Chicago is expensive, but it is one of the best places to invest in real estate.

@Bethany Travis, the short and straightforward answer is to pay a real estate attorney to draft a purchase and sale agreement with an exhibit to assign the contract.

That's possible, but expect a lengthy timeline and significant expenses.

Not sure what you mean about pay to play, but if you mean pay to be in a coaching program, it can be fairly expensive. 

The general rule of thumb for single-family rentals is the 50% Rule: that half of the rent will go to non-mortgage expenses.

@Karim WahbaSetting up a fund vs syndication for flipping homes comes down to scale and structure.Syndication: Typically involves a single asset, which can be stupidly expensive in terms of cost/time for just one flip unless it's a high-value property.

You get the benefit of the homestead exemption plus having tenants paying some of the mortgage (if you can find a fairly priced property...not easy in south Florida!). 

In my own personal finances, I do work with a fee only advisor - I pay him a fixed fee out of my pocket based on net worth, and he doesn't collect anything for investment in particular funds, particular brokerages, financial products, etc.

So I need to pay them off or keep them on the books and continue buying property with DSCR loans from now.