2007ish, in my country OS aired in the morning sometimes, AG in the evening (I remember watching episodes such as Charizard VS Articuno, during those days)... Then I guess I didn't really care about Pokemon for a while, then I discovered Gen V games... In 2011/2012 local Cartoon Network aired DP (despite BW was already being dubbed). So I watched a bunch of Battle Dimension, Galactic Battles and Sinnoh League Victors that way, watched some BW dub online.
Then, I guess ignored the anime for a little less than a year. Browsing YT with some people, we learned that XY was airing in Japan already, it had like 5 episodes, we got curious and started watching some uploaded episodes on YT lol, and I got interested in watching the Japanese version whereas the other guys were like "we'll wait for the dub". I've been watching weekly since then (at times I'd let episodes pile up because I didn't feel like watching). Since the final battles of the SM League I've been watching episodes live.
I've seen BW, XY, SM, and JN (ongoing) in their entirety. I recently finished Kanto (subs), Orange Islands (without subs, RAW JP) and currently working towards finishing Johto and AG in their original forms (the JP dub).