I think when you specialize you will always run into this situation. I work a lot with pipelines and I'm worrying that my knowledge about rigging and engines withers away.
At least with Max you're now in a nice position to get back into Python: Max now supports it.
> My biggest fear is python. I love it, but i fear it's "too easy" and becoming a saturated skill
Yes and no. Python is easy to learn but hard to master. While it's probably easy nowadays to pick up a "Python guy" it's still difficult to find someone who is a Python guy who knows software engineering (i.e. the topics Rob Galanakis posts about: testing, TDD, architecture, dev lifecycle, etc.) in the context of 3D production. i.e. somebody who can design robust, maintainable, scalable and future proof systems. Those people are rare, vs. the masses who can clobber together quick throw away scripts. I know pragmatism is important but imho we're still programming in a way too wasteful manner where the wheel is reinvented on a daily basis.