You could maybe level and gear all the way in 20 days (if you play nearly nonstop), but trying to complete the story in that time would essentially be throwing away the entire Realm Reborn game, as you'd have to skip all the storytelling.
There's nothing special about when Heavensward releases except that those people who have already finished everything currently available will get a bunch of new stuff. If you haven't finished what's currently available, then it's new as well so far as your game is concerned. Play the part that you're at. When you reach its conclusion that should lead you towards Ishgard, that's when to get the expansion. Don't worry about Heavensward until then unless you want to switch to playing an Au Ra.
I could maybe see someone who doesn't like quests or stories and plays MMOs exclusively for the end-game raids wanting to race ahead to get to the end where most of the raiding is taking place, but that really doesn't sound like you.
As for getting enough people to complete the required group content, that shouldn't be too much of a problem. Just like we now get level 50 players running the level 15 dungeons (level-synced down to where that's feasible), after Heavensward comes out we're going to have level 60 players running the level 50 ones. SE puts in plenty of rewards and incentives to make sure people still keep playing all the required group content. In addition to that, there will always be new players, players starting new characters, or leveling up additional classes/jobs. And, since the expansion is a separate purchase, there will be people who don't get it and continue playing A Realm Reborn by itself without Heavensward. (I personally will fall into the "players starting new characters" part of that, since I'd rather start over with a new alt in order to play an Au Ra than have to change who any of my current characters are.)



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