Downtown Baltimore. Nothing against Baltimore, but I groped in a bar there, so don't have any plans to go back anytime soon.
having been there for the AMS conference, even in the "safe/bougie" areas of downtown I felt unsafe traveling alone and constantly looked over my back during the mile walk to my hotel from the convention center. One night I tried to stop by CVS for some ibuprofen because of some killer headaches and it turns out they only let like 5 people in at a time then lock the store to prevent theft. Not even the bad parts of NY I visited were that bad. I think I have to agree here.
Tallahassee, I guess? All the one way streets are grating. I tried to Uber downtown when it was possible because parking was always hard.
this is up there too, went for a college tour and left early in part because the whole place reeked of sewage.
adding to the college tour list, Starkville MS felt like stepping into a Klan rally as soon as we left campus for lunch.
of course my old hometown's "downtown" was kinda depressing but it's not a city, so I'm not counting it. At least there it was just kinda a downer rather than outright hostile.