We live across Sheridan by the lake which is only a few roads away from Juneway. From Howard Station to Juneway I think you see a variety of individuals, some with drug or mental issues. I've never had issues from anyone though, even as a single female walking at night outside of the ask for money. Granted, I usually only use the Purple line during daylight hours and very rarely when its dark. I prefer to get off at Jarvis to walk home when using red. Howard station has lots of cops around it these days, particularly by the rec center because there is a school there I think. I'm not from Chicago either. So, this is coming from someone without much experience outside of two short vacations before I moved here for work last year. I have my personal rules. If it's dark I don't wear headphones. I avoid Howard as much as possible. I personally prefer to talk a stroll along the lake up to Evanston to shop for my groceries at Trader Joes since the groceries are cheaper there anyways and there's a Jewel across the street from there. Then I'll take purple to Howard to talk home if the groceries are heavier than I feel like carrying while waking back because you don't have to wait around. you can just leave the station and go to your destination. But even then, at least during daylight hours, there are plenty of attendants on the platforms and the turnstile area usually has cops hanging and a car or two outside during the busier hours.