Your realtor can give you all the actual sales comps to help you see the difference between the listing price and the actual sales price.I however do have a little contrarian advice. 

Run credit and background checks, actually call the listed referrals, and ask for bank statements.

Of those two, I actually like the first one better because you have a competitive advantage to that market and the amenities you could provide.

It also scrapes MLS for properties sitting 90+ days and reaches out to sellers who might be open to creative financing.Another big one: it sends out offers in bulk, tracks responses, and helps me focus on the ones that actually move forward.

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth. 

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

I liked the 3D model of the actual room enough to lease.

However, you can actually end up in a spot where you have no Federal Income Tax, but you still owe Self Employment Tax. 

Though it may cash flow well based on their current debt service, when you compare the income it produces to the equity they have is it actually even a good investment for them from an ROI perspective or would they be better off liquidating and redeploying?

We actually have a project wrapping up in mid city right now.