To me one of the few benefits of WIN32 is the fact that a single binary program can be used for all WIN32 opertating systems.
I am very keen on this as I use Microcross XTools, which is another Cygwin based tool but has an incompatible cygwn dll to the rest of the Cygwin world.
I also need to use GCC and OpenOCD for Philips LPC development and the two Toolchains just will not work at the same time.
The answer is Native WIN32 in the form of WinARM and Native WIN32 OpenOCD.
I do not mind helping with backporting this patch into the official source tree if that will help.
I run Ubuntu 6.06 at home and XP at work, so I can somewhat test both camps.
Keep up the truly great work Dominic, It is a major contribution to the Embedded development world.
On a different matter I hope Tsvetan can see his way to sending you a Philips LPC 3000 based dev board soon