The tipping point for crime was around 1996-1997. After that, murders (while a bit higher) were much closer to current levels.
After that there was about a 12 year period (until 2010) when rents weren't nearly as high as they are now -- around 40 percent lower across the board; and some neighborhoods have basically "flipped" and seen their median rents double.
The point is, from around 1998-2010 the city was about as "desirable" as it is now -- but significantly more affordable. To get affordability back to those levels -- we'd have to see something like a 30 to 40 percent reduction throughout the system.
It seems unlikely that would happen, even given the most ambitious upzoning, and the most wildly optimistic increases in inventory anyone could reasonably hope for.