I played for a couple months. Got my White Mage to level 50, I think was the max level at the time.. Then decided to stop playing for whatever reason. I guess mainly because I couldn't find people to play with. I see the new expansion comes out and I'm really interested in playing that new healer.. But I heard you need to do all the main story quests to reach the new expansion content? How long would that take someone who will be casually playing? Since I'm currently heavily invested in Legion right now.. Just looking for something to play on the side.
Well.. depends on how far you got in the 2.x patch chain, if you got through it. Good for you, Heavensward is rather easy to plow through in comparison to FFXIV, and you've a few months to do so which shouldn't be impossible.
If you didn't be ready for many quests sending you to middle of nowhere and back for little to no reason, I'd suggest netflix on the side. At least til 2.3-2.4 kicks into gear.
Thankfully, Heavensward is very streamlined, with a chance for you having to do a dungeon or two every now and then to reach the MSQ- level requirements to progress, but all in all, it's a smooth experience
The main story will take you quite a bit of time to be honest. Starting at 50, depending when you quit, you would still have several hours of lvl 50 story to complete before you even move on to HW content.
I will not sugar coat it, there is a lot. In ff they actually care about telling a good story and it gets a lot more interesting in in 2.5 content and beyond. If you want to play it casually for story, go ahead, take your time, you should finish by the expansion. But make no mistake, it will take effort.
As for finding people to play with, the latest patch brought cross server to the party finder, so now more than ever it is easy to find groups to do the raids.
If you left off after completing the main story in 2.0, you'll have a ways to go:
~100 level 50 quests that were patched in from 2.1-2.55
HW MSW from 51-60 is roughly another 100
Story quests added from 3.1-3.5 (roughly 40-50 now, can't check wiki currently)
Friend of mine started playing the game 5, maybe 6 weeks ago, and is now around the level 53 mark in the HW main story. That's someone who started from scratch, and not being able to play every day. With moderate time/effort, probably looking at a month to get to 60 (from where you are starting), maybe upwards of 2 months if you're really casual about it.
Your best bet is to get in and start doing it. It really doesn't matter if it's 50 question to 200 quest. Just get in and start working on it and you'll have it done in time and before the next expansion.
Edit: Also, it's Final Fantasy.. the story is amazing the characters are amazing and the events are very emotional!