I've had many of the same problems you describe. I haven't solved them all, but here are some things that have definitely helped:

Setting up CPAN

The first time you try to download cpan modules using perl ("perl -MCPAN ...") it will lead you through a setup, asking lots of questions about where different resources are located on your computer. If you answer these questions incorrectly, your CPAN client won't work. But, when you start it again it doesn't prompt you to change settings. To fix this, you can go to the directory "x:\(perl-path)\lib\CPAN" and delete the file "config.pm". Then the next time you use the CPAN client it will ask all the setup questions again.

The CPAN client wants a whole bunch of tools that you may have to download. The problems I've run into here are that some "unzip" and "tar" programs are not 100% compatible with CPAN. Be sure that the programs you're using know how to deal with Windows NT long file names. Most perl modules contain files with names that are illegal under the old DOS eight-char-name-three-char-extension standard.

One solution that worked well for me was downloading CYGWIN, a Win32 unix emulator with Win32 versions of lots of the normal unix tools like gzip and tar that the CPAN client needs. To get the tools to work under a Windows NT command prompt, you have to copy cygwin.dll to the system32 directory.

Tally