I don't have any experience with that one though.Specifically, for your househack ensure you're not commingling funds as you mentioned.

You just need to make sure you take a few important steps on the front end of the purchase to ensure they go smoothly. 

@Jeff Dzado get the paid version of Airdna so you can ensure you’re looking at the whole picture (although Airdna is not gospel, the data is getting better all the time).

You'll also want to ensure you have a good property manager to look after the upkeep of the property if you are not there to notice anything deteriorating or which may need attention.This article goes into a lot of the considerations about whether to form an LLC or not: https://www.mmpph.com/wp-content/uploads/2019/04/May-2019-newsletter.pdfCreating an LLC in California would cost you a minimum tax of $800 every year.

Chicago might be the place, just ensure multiple factors support the decision. 

But if it is, I don't see the upside to a buyer not using a buyer's agent -- it likely won't cost you a dime, and you will have someone guarding YOUR interests, and handling the coordination of the many, many aspects of the transaction to ensure a smooth closing. 

This will make the appraiser’s work more manageable to get done and will ensure that nothing is missed in the appraisal. 

Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.Don't buy in the roughest neighborhood in the urban core.

Overall, it sounds like you're in a good position, but ensure your education and knowledge base is up to speed, or partner with somebody who has a lot of experience. 

What are some clauses I could put in the lease to ensure I can sue the owners directly for non-payment of rent rather than the business?