you aren't implying that dependency hell is a problem unique to python/pip are you?
dealing with dependencies is always step 2 for me when learning a new language and dependency hell seems like a universal problem. I could be wrong though.
Honestly, Maven is way easier, more powerful and works identically on Win, Linux or Mac. The key is that Java let's you set classpath as a command line arg and pythonpath is an environment variable.
IMO, buildout is more like maven for python. but again the tools solve this problem of "dependency hell" which to me is a problem all languages have, not just python
dealing with dependencies is always step 2 for me when learning a new language and dependency hell seems like a universal problem. I could be wrong though.