Out of curiosity, I finally bit the bullet, installed 64 bit Ubuntu 8.10, updated http://wiki.winehq.org/Wine64 to show how to build gcc, and built wine with win64 support enabled.
It built successfully on the first try, but starting any conformance test or win64 app fails with wineserver: request.c:744: open_master_socket: Assertion `sizeof(union generic_request) == sizeof(struct request_max_size)' failed.
I tried grabbing the patch that seems to fix that, http://repo.or.cz/w/wine/wine64.git?a=commitdiff_plain;h=6e77a4879d5e62a9777... but then I got other errors.
What's the minimal set of patches needed to start trying win64? I'd rather not pull Maarten's whole repo, I have no idea how closely that tracks winehq... - Dan