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I’ve been lookin at real estate in that area as well, 250-300k might get you a place that hasn’t been renovated since the 70s and needs a ton of work. Realistically need a budget of 350k+ to get anything that isn’t falling apart imo. You might have better luck in the area around Garfield Park, definitely less gentrified but also not quite as safe.
I just moved to Garfield Park a few months back and yes, there is a homeless population around the park but that’s also true of downtown, near north, etc. I’d highly recommend checking it out, after looking for a long time on the east side, I’m actually very glad I expanded my search because I have more access to green space, a library, farmer’s market, 65 (one day), etc.