Path seperator for the -Xbootclasspath command line parameter to java.exe on Windows need to be ';' and not ':' as is the case for *nix apparently. This is a problem in the *.properties files driving Ply. Note that in the ply.bat runner script the seperator is in fact ';' and that seems to work fine.
Fix is just to alter the *.properties files, replacing ':' with ';' where appropriate.