I mean, if they follow established trends, next up is the Ruby/Sapphire remake, followed by the third version of/sequel to X and Y, neither of which offer that much room for screwing up.
Only issue is there is no established Trend. There isn't a set pattern for remakes, and they have already broken the remake cycle by not introducing a remake in the last generation as well as broke the normal cycle by introducing two sequels instead of a third version/director's cut.
All the hints towards a remake were all over fifth Gen if you believe that they were hints at all and we didn't get them. For all we know, when Gen 6 is over, we'll wait 3 years for something new from Gamefreak and move straight into Gen 7 on the next possible Nintendo based Handheld system...which I hope to the high heavens doesn't happen....They still have a lot of milking they can do with the 3DS.
Even still we've already been given the hint that there isn't any specific pattern to how they work. They pretty much just start on the next thing fairly randomly and if anything from Matsuda's special announcement is apparent...they pretty much pick their inspiration randomly.
Anything can happen with this set. We can completely forget all that we are used to getting, having this Gen still make incredible sales...and then move into the next Generation of Pokemon, or they can milk the generation for a while, producing one or two more titles to push it forward and try to stretch the time in the generation with more remakes....though at this time, all of them will need a remake due to them all being graphically inferior to current set up not to mention Fairy Type would have to be reinstated into all of the early games, similar to how Steel and Dark were reinstated into Red and Green with the remakes.
I could see a few side by side remakes in the up coming years, Gens 1 and 3, and then Gens 2 and 4. Gen 5 is pretty close already and isn't as far behind as the other four are. Only reason to remake them now would be for updating all the new info, despite that none of them may include new battle mechanics from the newer games outside of maybe PvP match ups over Wifi. (Triple and Rotation...I don't think Sky or Horde will be outside of main game as of yet.)
This can all still happen in the next 3 or 4 years too. There are a lot of roads Gamefreak can take from this point. Some good, some not so good, though none of it will really kill the company. We as fans will buy the games no matter what. Though it remains to be said...Gens 3 and 1 are still in the same boat as far as connectivity is concerned as well as need to update. If anything I hope both are done within this Gen if they are to be done.