While there are quite a few dimensions to the problems with the current landscape of West Chapel Hill Street, one of the more egregious ones is the interchange with the Durham Freeway. On the north side, the interchange is 707 feet wide (0.15 mi); on the south side it is 382 feet wide (0.07 mi). This is a huge, gaping hole in what was once a continuous streetscape.

So what to do - get rid of that pesky Durham Freeway? Nah, this is only mildly radical idea day. While I think the Freeway was ill-conceived and has cost Durham more than it has gained Durham, I recognize that it isn't going anywhere. So while I think it's instructive to look at the decisions that led to the Freeway (particularly when some of the same ideas go into similarly ill-conceived projects like the widening of Alston Ave., or Eno Drive,) the focus should be on how to minimize the Freeway's negative impact on the landscape. Because right now, no one is trying very hard to do that.
So, what, more flowers on the roadside? No, not good enough. I'm a fan of landscaping, but it is kind of an-aspirin-for-your-amputation when it comes to the Freeway.
I've always been fascinated by the idea of a modern-day London Bridge (not the one in Phoenix or wherever) - with buildings lining the side of the bridge. Then, about a year ago, I read about a project in Columbus, OH called 'The Cap at Union Station' that did just that.
Building something over the freeway isn't unique - big modernist structures spanning the freeway have been around for awhile in several large cities. What makes this project innovative is that they have turned a freeway overpass back into an actual streetscape by combining innovative reuse of wasted space with great design.

Aerial view of The Cap.
(Melaca Architects)

Corner view of The Cap.
(Melaca Architects)

Streetscape view of The Cap.
(Melaca Architects)
Streetscape view of West Chapel Hill St., looking west.

The West Chapel Hill St. topography is such that the overpass would be well suited to structures on either side of the overpass, spanning the Freeway. For the parking worriers, I've filled in potential space for parking in grey.

An even more ambitious proposal would extend the 'cap' on the south side back to Jackson, or even Vickers, thereby reconnecting the grid. But this requires closing or figuring out what to do with the eastbound on-ramp. While this is hardly infeasible, it moves the project out of mildly-radical territory.

Beyond Vickers, the topography changes significantly as the Freeway moves into the streambed of a branch of Third Fork Creek that runs in the woods near Gregson and Jackson (which is culvert-ed under the Freeway and, I believe, re-emerges behind JJ Henderson).
Must be talking scary costs, huh? Well, what I've read about the Columbus I-670 cap states that the cost was $7.8 million. For those counting, that's somewhat less than 1/6 of a Performing Arts Center. If it costs $18.5 million to fix the Loop, as per Bill Kalkhof, that means that we could build a cap at Chapel Hill St., another at Fayetteville St., another at Mangum St. (or Swift), and fix the Loop for about the same price as the theater.
I'm not suggesting that we run out to spend another $44 million. I am suggesting that when we talk about spending huge sums of money, fixing our infrastructure problems should be on the table. My opinion is that repairing some of the damage caused by the Loop and the Freeway would do more for the overall quality of life of the people who actually live downtown and in the near-downtown neighborhoods than the Durham Gritty Performance Center.