So I went through a few weeks where I was diligently hitting the world boss on each max level toon, working through both the Arathi and Darkshore Warfronts on the toons that were able to on each toon in the interest of gearing those toons up, and I made some decent progress over those weeks across all of my max level toons.
I do have trouble figuring out why I'm bothering. I'm assuming there will be the normal late stage gear pinata at some point in the expansion that will let me quickly catch everyone up with substantially less work.
I finished up the Battle for Dazar'alor raid on both an Alliance toon and a Horde toon and have caught up on the War Campaign on both sides. It was a bit disappointing that the final Horde quest in the chain clearly had some serious bug issues. It's probably only an issue when a lot of people are doing it at the same time, so it's possible they decided they just didn't care.
For any of you that might be getting stuck on that quest, what finally worked for me was hitting /reload as soon as Baine started his second piece of dialog.
I've also been leveling the rogue. I wasn't finding subtlety nearly as fun in this expansion as I did in Legion. I tried Assassination for a while before finally settling on Outlaw. Since my rogue is also my engineer, I should probably just do more PvP so that I have more marks for recipes later on, but so far I'm just doing the normal leveling thing.
Next up, after the rogue hits max level, will be the druid on the alliance side. Plan is to level him as feral, but we'll see how that goes.