Investing before a Downturn

[Nick Weston]

I am looking to purchase my first rental (first investment in general) and looking for advice. I am getting skeptical I am not doing the right thing due to timing with a looming recession. Coupled with that I am in Chicago so the price point is high. I am in my first year out of college so I don't have a ton of capital. Tax law in Illinois is ridiculous as well.

My gut reaction is "just do a deal". There are always reasons it may not work out, so I am leaning towards just finding a property I know will cash flow and doing a house hack -- even though I see a lot of negatives regarding timing and location like I mentioned. 

Does anyone have any advice or thoughts they could share? Thank you!