Chicago - a good place for buy and hold?

[Rob Bianco]

I'm not exactly a beginner; I have 30 units in Kansas City, but I'd really like to diversify my investing and I really enjoy the city of Chicago. Despite all the headwinds the city faces, I really believe Chicago is a big winner in 15-20 years to climate migration. I've looked at numerous properties online, inside the city and also in the suburbs, and the returns look OK on paper, but gosh, those property taxes seem to fluctuate wildly. I've heard some pretty horrible anecdotes about getting a bill that's anywhere from 20% to 120% higher and as an investor it's really hard to reconcile how that affects your investment and how investors react to that. 

I'm really trying to understand the investment strategy: Usually, in Kansas City, if my bills go up (tax/insurance) then I raise rent marginally to cover those costs. I try not to raise rents on good tenants if I don't need to, but in Chicago, if my taxes go up $100/month, do you just jack rent to meet those costs regardless of how good a tenant is? Is the thinking that someone will ultimately pay it, even if the tenant moves out? Do people find turnover to be high in the city? 

I grew up in NYC, so rents going up was never unexpected, even if it was $100-$200 per year, every year, and if you bought something in the year 2000, I imagine you'd have made a fortune if you still owned it in 2022 and I'm sort of hoping for a similar experience with Chicago. 
 

Half the people I talk to about Chicago say it's in a death spiral and the other half say it's a great city, and to come on down, the water is warm.