“Does it become sketchy immediately south of the UChicago boundary or are there areas of reasonably OK student housing just outside the campus?”
There must be students living in Woodlawn - 61st to 63rd at the very least looks a lot better now than it used to. Woodlawn Commons will be yet another UChicago building fronting 61st.
There are just a LOT more students and families all over Hyde Park and the surrounding area now. One definite advantage of increasing the size of the college 