ChadFowler.com The Big Rewrite
I've been involved in a number of "big rewrites" over the years. The Suneido project could be called a rewrite of a previous in-house project called C4, which in turn was a "rewrite" of a framework built on top of a personal information manager called Lucid. Our accounting applications are also the third rewrite. So it is possible to pull it off. And I would bet some of Chad's projects have succeeded in the end. But his points about the dangers and problems of big rewrites are definitely valid.
Joel Spolsky calls the big rewrite "the single worst strategic mistake that any software company can make"
In the end it comes down to Software is Hard