Actually, I don't expect that the Win32 will constantly break once the
bulk of LLVM is converted over. LLVM needs precious little support from
the operating system. A few fork/exec here, a little mmap there, and
some file/path support. That's about it. It may grow overtime, but if
we're using a lot of the operating system interface (any operating
system interface), we're doing something wrong.
I'm the last person who can raise his hand and speak about the LLVM project but... I feel you are totally right.
IMHO there's a big difference between aiming to port the whole framework to Windows and porting only the very-core-stuff (TM;)
Porting the using-the-jit example, have to be trivial in the sense that you must be able to use the core-stuff in such an easy way, apart from platform differences.
MinGW is a more radical (and efficient) port of the gnu compiler to win32. It does not require any cygwin.dll and try to rely less on emulation. It's distributed with a minimal bash support and common *nix tools. Actually I feel that is probably more difficoult to adapt LLVM to it, but not SO different to the cygwing port. Summa summarum it has the advantage of producing standalone executable without external dependencies.
I agree. Chris made a good point in that there shouldn't be anything
wrong with using cygwin for the build tools but compiling our libraries
so that they make use of native windows calls rather than requiring the
slow cygwin.dll. That would make our tools work much better on windows
and it would not be terribly difficult to do.
I think that MinGW is a better alternative to cygwin on windows....
I think this is where we use cygwin which has already been shown to work
with our makefiles.
Also with MinGW you have all the build tools chain... but alas, someone must try it 
That told, building the LLVM with the microsoft compiler is another matter. I'm interested in building the backend, not the frontend tools (hoping to skip a lot of problem related to signal-paths-and-portability-mess), because I want to play with the 'compiler-infrastructure'. Actually the MS C compiler is a GOOD compiler, very compliant and efficient, and has the BIG advantage that is compiles with the defacto-standard MS C runtime...
I'm very busy in these days... but I hope to send other VC patches soon.