Yeah, because I would love to spend my time maintaining something that is no longer supported, while my skill set slowly goes the same way as my will to live.
You really need to badger your managers to upgrade things every couple of years or so. If you do it continually then it is not going to be as painful as jumping a couple of releases of the language in one go. Unless you do new stuff and use the latest technologies then your working practices are going to remain the same. Things move fast these days (though not that fast in the python world). To reference a language I am more familiar with, I am sure a C# application written in