Finding a middle ground of building a roadmap to refactoring your way forward is often much better.

Appreciate the Joel link, nice to see that kind of stuff again.

With that being said if it's the same small team that built the first version, there can be a calculated risk to driving a refactor towards a rewrite with the right conditions. I says this because I have been able to do it in this conditions a few times, it still remains very risky. If it's a new or different team later on trying to rewrite, all bets are off anyways.

We have to remember 70% of software projects fail at the best of times, independent of rewrites.