@DunBoyer Thank you for your insight.
The gentrification of Woodlawn has already started. Just out of curiosity my wife and I are checking out the real estate market of Woodlawn online and we are surprised to see many new houses being built and sold. Smart money sees the potential of Obama Library and is already buying lots and building multi-unit buildings. I would guess the expansion of U of C southward is just a matter of time despite the agreement with the Woodlawn community. In another 10 to 15 years a much more affluent Woodlawn community may even welcome an U of C expansion.