The whole arguement for wanting to 'skip' everything up to this point is for one reason: end game. Many new players just want to be where "the cool kids are" and are not interested in running errands for the three cities at the start, or throwing in their lot with the Scions, and so couldn't care less for the story anyway (an attitude unfortunately fostered by too many MMORPGs whose stories are usually little more than window dressing at best and excuse plots at worst, and so these players cannot understand why and how FFXIV is so story centric and focused.).

And this leads to my belief Yoshi probably will not end up going through with such an idea: they already sell story skips on the Lodestone, and so allowing players to skip to DT would completely invalidate a lucrative income stream to SE (no doubt the actual revenue gained from the story skips probably will play a part in Yoshi's decision).

And one last thing to remember, we already have players complaining they missed out on 1.0's story and requesting 1.0's story be brought back somehow "to get the full story", and yes, there has been incidences here on this very forum from players who bought a story skip, then eventually regretted it due to missing out on context, just like how Cleretic mentioned above. If Yoshi did implement this, I can only imagine the complaints from players who wanted to skip ahead to endgame, then found it fleeting and realized everything they'd missed out skipping ahead in the first place, and wanting it to be reverted, and being unable to. It's just easier to keep it as is, personally.