To be honest, im not sure I want to go into the newer generations. Seems like so many new features that it kind of took away from the simplicity of the pokemon games that I'm used to.
Pokemon ORAS does intrigue me a bit, I might go that route or stick with Soul Silver/Heart Gold.
If you're playing a remake, you're already pushing past whatever "simplicity" existed in the original game. FR/LG is much more complex and polished than Red/Blue was. HeartGold/SoulSilver is heavily built up from what Gold/Silver/Crystal were.
If you play the remakes, you're also playing up to whatever complexity level existed in the corresponding main games from the generation. If you could handle HG/SS, you could also handle Diamond/Pearl/Platinum. If you played FR/LG, you were up to the level of playing Ruby/Sapphire/Emerald since the remakes always remake the classic game to be equivalent in terms of play style and complexity to the non-remake game of the same generation.
So if you play ORAS, you're up to speed to be able to handle whatever X/Y throws at you.
and really, it's not like it's
that much more complicated. Since Gold/Silver there's only been 1 added type (Fairy. Weak against poison and steel, strong against dragon, dark, and fighting, immune to dragon type attacks), a couple more multi-battle types (rotation, triple), and the fact that TMs are now reusable. And stuff you'd have already experienced like the addition of new mons, moves, and abilities.
If you've made it to the 1st set of DS games, you've already experienced the biggest changes the series was going to throw at you (the first type additions and the splitting of attacks into physical attack and special attack based on a move-to-move basis instead of by type)
