Yes, people are still using Airbnb but if you are basing your main long term investment around it I would really consider other exit strategies and alternative monetization

It allows units and would be a less expensive alternative to FHA when it comes to mortgage insurance, particularly because it can come off after the mortgage gets to around 80% loan to value. 

@Christian NachtriebThe big brokerages do not allow for investment into alternative assets such as real estate with their plans.

Your MIL might consider a tightly structured Joint Venture with a local developer as an alternative.

what other alternatives can I pursue in looking for a deal out here in Chicago.

As an asthma sufferer, I too wanted to find an alternative. 

@Tony Wood, I don't believe you can view the MLS without a realtor or a license, however I would suggest realtor.com as an alternate.

like a Google Docs is there an alternative to QuickBooks ?

Alternatively, look up the owners of local self-storage places in your area and reach out to them.Best!

As a high income earner, there are alternate routes that garnish high returns than LTRs, are more passive (nothing is truly passive) than both LTRs and STRs, AND expose you too much less liability.