Cost of Rents - Lower than Expected

[Morgan Van Ness]

My apologies if this is a stupid question, but something's been bugging me for the past few days and I can't seem to find an answer for it.

I've been renting 2-4 bedroom units in Chicago for the past 12 years and recently have moved towards buying a multi-unit place for House Hacking. Now I'm just getting started and have only looked at 10-20 properties on the MLS thus far, but EVERY single unit is charging rents FAR lower than I ever paid as a renter. Obviously there are several issues at play here, as not everything is a true apples-to-apples comparison and it's quite possible that many of these units are rented to family or long term renters, but the discrepancies are off by often $700-1200/mo. Is it possible that I've just been overpaying my entire life and don't have a true understanding of market value? Or do many landlords not put the effort in to bring their properties up to market rate?

Keep in mind I'm very new to this.  Would love someone to open my eyes a little further!

Market: Chicago, north side

Avg. Rents Seen for 2BR 1/2 bath: $700-1300

Avg. Rents Paid by Me: $1400-2500