Advice on the Chicago market?
I'm a student (graduating soon) who inherited a home in the western suburbs of Chicago back when I was 18. I got some great experience hiring contractors to fix it up, rent it out for a bit, and sold it this past summer due to ever rising taxes. I'm likely staying in Chicago proper after graduation for employment (assuming a decent offer) and would like to carry on investing.

Based on my research however, this is not the time to invest in Chicago. I've looked at public government numbers on job growth, which is slowing down, and rents seem to have plateaued at their high. Taxes are still ridiculous, and the state can barely get a budget together. There are some significant developments being built in the city but demand to live here doesn't seem great. I'd be buying &lt;5 unit residential buildings (probably just one for myself and renters to start) under an SLLC that I would manage (probably with a PM for at least the first year to build a network of tradesmen), but I'd rather not throw money at a bad market. 

Is my basic analysis correct or should I be less worried? I know that while a city can be slowing down, certain neighborhoods can trend upwards (Logan Square for example), but my time and resources are limited to hunt for hours everyday for a good deal, especially with the stress of a job hunt. 

Extra details: I'm also currently invested with an FA (I know, fees are bad, but the performance is great) and this would significantly change my investment profile. I've reached out to some pros in my network who think it's a cool idea, but I got the "just be careful" talk as well. I want to start my own business some day but this may not be the time.
[{"id": "dopii6l", "text": "The analysis is spot on, the city is in a bad spot right now, but things are improving in small pockets. If you buy well, renovate smartly and use modest leverage, you protect yourself as well as you can. If you're looking nationally then don't mess around with most of IL compared to other markets with better demographic trends. \n\nIf you're set on being here, then do what you can to get the neighborhoods on the upswing. That's why I bought and renovated an apt bldg in Logan, I'll let you know 20 years from now if it was a good decision. ", "replies": [{"id": "dounsbk", "text": "&gt; fix it up, rent it out for a bit, and sold it this past summer due to ever rising taxes. I'm likely staying in Chicago proper after graduation for employment (assuming a decent offer) and would like to carry on investing.\n&gt; Based on my research however, this is not the time to invest in Chicago. I've looked at public government numbers on job growth, which is slowing down, and rents seem to have plateaued at their high. Taxes are still ridiculous, and the state can barely get a budget together. There are some significant developments being built in the city but demand to live here doesn't seem great. I'd be buying &lt;5 unit residential buildings (probably just one for myself and renters to start) under an SLLC that I would manage (probably with a PM for at least the first year to build a network of tradesmen), but I'd rather not throw money at a bad market.\n&gt; Is my basic analysis correct or should I be less worried? I know that while a city can be slowing down, certain neighborhoods can trend upwards (Logan Square for example), but my time and resources are limited to hunt for hours everyday for a good deal, especially with the stress of a job hunt.\n\nThis is mostly true, but an oversimplification. Apt sales are at record highs. There is a lot of new construction and some neighborhoods, like the West Loop are red hot with all kinds of redevelopment in progress.\n", "replies": [], "depth": 2}], "depth": 1}]