another little cygwin gem (pun intended): if your webrick starts but outputs nothing, and never binds to a port (going through the sources reveals that it just hangs in a backticks shell command call, but works fine if you run it standalone without any rails stuff or pass your server script webrick as an argument in command line); if you get bizarre memory relocation/unable to remap fatal errors when running rake, then try the following:
- shutdown/exit all your cygwin processes
- run ash from start/run (it is under bin\ash in your cygwin directory)
- then run
rebaseall
this solved it for me. see this post for some details.
this cygwin/rails setup is a bundle of joy, i tell you. never a dull moment on these lovely long winter nights.