Any big city is kinda sketchy, imo. that's why I tend to avoid them. Lots of tweakers, and very few good spots to sleep makes it wayy more dangerous.
Pretty much sums up this thread...It's common sense to avoid the cities mentioned in this thread. I tend to like to stay where homebums won't be, like at all. Which is probably the main reason I rarely run into travelers (hitch hiker ones) but I'm ok with that if it means I can stay away from trouble as much as possible. Sometimes I do have to bite the bullet and rush thru a big city but I won't stop for breaks or anything that day. As long as you wake up early when the normal people are going to work, and get thru the city before 2pmish, it's all good.
That being said, Chicago I stayed near the water, but apparently still took me 3 days because I had to avoid the south west at all cost and go around going north lol, still a ton of homebums but I bet not nearly as bad.
Jacksonville FL, This one was pretty easy since I had my bike at the time but still North Jacksonville was pretty ghetto and didn't help that my dog was snapping at every 'gangstas' feet, luckily I the worst was just a very angry stare down. Downtown was ok but the North side was sketchy as fuck. I was probably being more paranoid but just really felt uneasy...Also the cops are dicks....you know it's a shitty area for travelers when I got kicked off property twice for charging my phone aka "stealing electricity" =/ . Which is why I tend to ask the clerks and store managers now days just so I can feel comfortable.
Albuquerque NM, This was an ok experience, never felt threatened or uneasy and people were generally nice but the homebums were everywhere and was littered with trash 360 degrees. I got my electronic bag stolen but that was my fault I guess. Felt like using the tarp that night and I guess it was sticking out? Not sure, but it was gone the next day and fond a few chargers spread out about 20 feet from where I was sleeping. So I guess a little off topic but there's a reason why I keep moving even if I see one homebum in a town or city, just don't trust them and tends to make me look bad as well lol....Probably came off as a douche by saying that but idc, think most if not all travelers agree we have standards when it comes to meeting new people on the road....mostly just a quick look at gear, hygiene and the way they carry themselves, neatly packed and organized...pretty much not walking around with a shopping cart and looking all depressed.
I will say this, There really is no bad parts in Colorado, almost laughable when people told me to stay away from this and that bad area lol.....I mean it's Colorado...
Anyways, sorry for the rambling...but it's just common sense to stay away from places like Detroit or Chicago, and if you absolutely have to go thru a big city, ask around or Google what are the bad areas, usually the south parts, and stay on the outskirts if possible or leave extra early before all the tweekers start running around the streets, walk fast and no breaks lol.