Thanks for the replies, everyone! Yes, after rewatching some AG I definitely agree that, aside from nostalgia, it can be difficult to watch since it was catered to a pretty young audience. I just started watching Best Wishes and I find it to be a little more mature with Team Rocket and just more traditional anime features (Oshawott's facial expressions, etc). Still fun though, and the movies definitely haven't lost their charm. Plus, I forgot just how awesome the season 7 opening was.
Definitely! As much as BW has evolved, I really miss the chemistry between Max and May compared to Cilan/Bianca/Iris. The latter three really just seem to individually respond to Ash/focal points of the episode, whereas May and Max really had their own conversations and storylines.