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Martin v. Loewis's reply on c.l.py:

Since you are asking for a work-around: cd into one of the 
more nested directories when the path gets longer 
(os.chdir), and use relative paths from then on.

If you want to study how to solve the problem: the relevant 
code snippet is in Modules/posixmodule.c

	/* the library call can blow up if the file name is 
too long! */
	if (pathlen > MAX_PATH) {
		PyMem_Free(pathfree);
		errno = ENAMETOOLONG;
		return posix_error();
	}

There might be different ways to approach this:

- challenge the correctness of the comment:
   - try to establish why the author of that code
     thought that the C library could blow up
   - analyse whether these arguments are still true
     with the current compiler version
  -or-
   - prove the argument wrong by analysing the source 
     code of the C library
- then remove the constraint
-or-
- use different API to achieve the same effect without
  suffering from the constraint.

I'm serious about these suggestions: users would appreciate 
if this gets fixed somehow - apparently, the system allows 
longer file names, and apparently, the system itself can 
deal with that quite well. This
can be only true if the system either doesn't use its C 
library, or if the C library does not have this restriction.