Is it difficult to transition? Yes, in that if you spend 10 years learning SystemA, then it will take some time with SystemB to build up to the _same level of expertise_ that you enjoyed on SystemA.
The neat thing about learning one OS or system _deeply_ is that the deep knowledge gifts you with frameworks for learning the next-system.
I wrote software on various *nix'es during my university time, then worked on OS/2 (yes, "OS-who?"), Windows, and now I'm at Google, (my work involves 80% Linux 20% Win). It took me some time to re-build my skills on each environment/platform, but it's been a great ride and a lot of fun.
(P.S. earhart@ pointed me to this thread, and says hi to all y'all: Evan, JonO, JVert, LandyW? Dan?)
Source: 33 years experience hopping all over the spectrum
Ultimately, it's all just code and problem solving. And you can usually find a way to leverage your expertise in one domain into a different domain.