@Seth Coronis :
"because sky high property taxes plus a mortgage would cancel out any profit. "
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"Profit" is a misnomer, since after taxes, a corporation should be indifferent to whether it is financed by equity or by debt. Same applies to people. Depending on your appetite for risk, you make your equity/debt ratio.
If you can get a better return on something else as opposed to the mortgage interest rate, then invest in that something else. If not, maybe you should be the one making the mortgages, not taking them.
As was pointed out, returns on A/B properties is tough. Prices take it all in A/B neighborhoods. Try a C neighborhood and look at buying into a well-maintained 4 to 6 flat or a similar sized condominium. One of the things to look for in evaluating C neighborhoods is whether it has a niche advantage that gives you a steady stream of tenants. For example, buying within walking distance of Midway airport gets you airline and airport workers (Flight attendants, etc.). Buying in certain areas around colleges can get you students, or -- select wisely -- young professors just starting out.
Chicago is tough on AirBnB because each alderman gets to set the rules for his own ward, and so what was legal yesterday is not legal today. Condo boards frown on AirBnB and its ilk also.