Functional Developer (What was Harelequin Dylan) was nice. The editor would syntax highlight the code based on the optimization level. In this way you could look at a method call and see if it was inlined or not and decide whether to seal functions or classes to improve performance.
Another interesting feature was the editor was written in Dylan (using a framework called Deuce). This was emacs-like and had features like virtual sections in a buffer that could each be mapped to a different file on disk. This allowed viewing in a single editor pane the implementations of all methods of a generic function even if they crossed multiple files. This could also be edited as if it was a single file.
Functional Developer and now Open Dylan also support debugging on Windows, have a REPL (on Windows) and many other features.
With the upcoming LLVM backend, we'll be able to bring those features to other platforms, but we'll need DUIM backends to support the user interface. That's a big part of why this call for help mentions several GUI related things.
With some luck and a lot of hard work, this will be a great year for Dylan.
We only implemented it for static optimisations I think (i.e. you could see at a glance how well the compiler had inferred types, resolved method calls, inlined functions, etc), but we had a lot of ideas at the time around its future application to profiling results, as well as layered, more interactive presentation.
It'd be a great addition to Light Table...