I would start it with one to three weeks before the games release so the people could get more excited about it. Of course one needs to balance the time, or what should be exciting may turns to be disappointing and long waiting.
Follow the signs of the Crimson Thunder
We will stay by your side
Let our voices be there to guide you
Well, we may not find out more until we start to get August's eps, or an ep pops up that was not shown to us in the previews. I may be taking the wording too literally, but Iris and Cilan are indeed going with Ash to Kanto. Key word: WITH. To me, this implies there will be another flipping saga after this one.
Step into the Fairy circle
I think it will end around the time of the new games release. First of all I think they want both the dub and sub episodes to be shown at around the same time, since the games are releasing at the same time. Don't you think it would be weird if the Japanese and American release of XY happened at the same time, but the anime in America still had a ways to go to catch up. I mean they did this in Advanced Generation, but still, they showed at least preview episodes. Right now they are only 93 days behind anyway. My theory is that they spread out the DA episodes to allow the English dub to catch up, since they take breaks during the summer anyway for movies and stuff like that. They may even skip a dubbing of DA in order to get in closer to the Japanese. I mean this does seem a bit unrealistic, but it is possible.
As for the dub skipping DA, that is ludricrous, they wouldn't do that. We're closer to the raw than what is indicated for that even if it does continue to October.
Step into the Fairy circle
Since we got that shot of Dento/Iris crying I assume the next stop is the new region.
Ash fan. Multi Ash shipper =]
Ash will go back to Pallet Town, repack, be ten again, and set out for a new region
This little Kanto ark is a lot like Battle Frontier, it's just a little something to tide us over until Gen 6 and the new region. I definitely think Iris and Cilan will leave. I wasn't sure about Cilan but now I can see him leaving. He's personality is too overbearing and he's very associatable with Unova. I think the writers will want to make a fresh start like they did with BW. It's interesting, when Iris was revealed, we were told she was a character made exclusively for the anime. I thought she might be the one who sticks around forever, or at least for a long time, then we found out she was a gym leader in the game and her days pretty much felt numbered.
After Da comes Pocket Monsters X and Y.
I think both Iris and Cilan will leave. I'm pretty sure half the reason Cilan replaced Brock was because Brock got stale, so why repeat that mistake?
Plus this might just be me but with them reintroducing classic Team Rocket and people like Tracey and the older style Jennies/Joys, I feel like they're trying to bring the show back to pre-BW so that the writers of X and Y can have their take on classic Pokémon rather than working with the changes BW made. Getting rid of Cilan would be one of the BW-specific things that have to go.