I remember watching Pokemon as a child and I'm keen to start up again from where I left off but I'm just mindblown at the sheer amount of content they've made. Something like 16 movies and about 800 episodes in the anime.
Has anyone here actually watched it all or ever tried to take on this task before?

I remember owning VHS tapes of nearly every generation 1 and 2 episode and movie, and I may do what you're thinking about doing as well, The main issue is finding the time for it, however.

Look forward to Pokemon... The Origins