Of course, it's always smart to keep funds aside for unforeseen or emergency related costs.Others who have already responded have provided some great opinions. 

Unless you have cash backing of your own to buy and a solid commercial buyer's list, these deals are unlikely to close.It doesn’t matter if I agree or disagree with the answer the responding poster provides.  

It’s more expensive than PropStream, but the data quality is higher.For ARV calculations, if you don’t have access to the MLS, our Backflip App can provide it (it's good).

The lifestyle question is one that you must determine, then narrow down what parts of Chicago provide you with that lifestyle, then we can really answer the question- How is the market doing in those specific neighborhoods?

Also provide tons of good / detailed photos along with property details critical for the investor to make a decision. 

They have a formula that works and provides them the rate of return that makes it worth it so, don't feel like you'll just negotiate them out of their shoes like you're Trump. 

Could anyone provide guidance on how to obtain the contact information of an underperforming host on Airbnb?

Hey Jake thanks for the feedback and providing a valuable perspective when consdiering this opportunity. 

The seller may need to be the one who talks to them or you may be able to talk to them directly if you provide them with a letter from the seller specifying the loan #, sellers SSN, etc.

Looking forward to connecting with others who can provide guidance, tips, or even potential partnerships as I dive into this exciting field!