The head vs. HEAD problem is a well-known problem with using CPAN on Mac OS X. There was some discussion on this list last month because some people believed that the problem had been fixed. Sadly, your experience proves otherwise.
Indeed, one can blame this problem on the unique characteristics of the HFS+ filesystem. Wherever the blame lies, however, the fact remains that there are now a huge number of machines with Mac OS X installed using the HFS+ filesystem -- perhaps more than any other flavor of Unix, if Apple's propaganda is to be believed. Case-insensitivity is here and it is widespread, and CPAN should be modified to take it into account IMHO. -- Dave