In my personal opinion, development on FFXV's extra content will be split into teams of 3.
One team is constantly working on Comrades, so we should see (hopefully) some significant updates there.
Another will be the DLC/Episode team.They are currently working on Ardyn/Luna/whatever that will be signficant content additions and changes to gameplay.
This is important because a 3rd team will likely not change gameplay and strictly focus on giving more to the base story and Noctis. I'll call team 3 the free content/patch team.
I can see the Comrades team filling in more of the gaps in the timeskip story, the DLC team adding more supplemental, world/lore material while bringing in plenty of new gameplay options, and a final team that I'm thinking will provide the content updates to the base game, namely chapters 9-12 and 14.
There are 3 reasons why I think this.
First, there are like 3+ directors now for FFXV, Tabata is involved but he is working on other stuff now. For example, there was the Episode Ignis director, the comrades director, and someone directing updates to the base game (think character switching, the free story update, multiple hunts, the festivals and more) There is more leeway to have other people working on multiple updates.
Second, Tabata has repeatedly stated that they plan on updating the 2nd half the game, even in the last game informer issue.
Third, and most importantly, I cannot see this new DLC being charged as updates to the 2nd half of the game. They must be separate if they want people who didn't like the story transition to come back. For all intents and purposes, DLC isn't going to bring those people back. Episode Ardyn is not supplemental to fixing the 2nd half transition, free content patches will be made for this. They must be implemented into the main game. This is why we haven't seen any additional, paid content specifically with Noctis. If they are going to open up Nifleheim or fix chapters 8/9-12 and 14, they will be specifically free for those who did not finish to try and play again. There will also be something in it for those who beat the game already.