Still, you must be aware of a few thing.
- Wine is not 100% byte order clean.
Alpha seems to be "correct" endian ;)
- Wine is not 64 bit clean. This is a little worse especially since Win32 often stores pointers in 32 bit integers and this problem really can't be solved in a good way, since extending the size of the storage is not possible at least not if you want to be able to implement a x86 emulator in the future. However I guess it will be possible to force all memory usage to be in the lower 32 bits of memory to be able to cope with truncated pointers.
Digital has(d) a lot of very good emulation technologies - FX!32 which let to run win32 386 apps on NT Alpha with almost full speed, em86 which runs 386 Linux apps on Linux Alpha (http://www.cs.rose-hulman.edu/~donaldlf/em86/index.html), x86emu which is used in XFree86 and MILO to initialize graphic card's 386 BIOS.
Regards, Nerijus